Scaling Tech – The blueprint for successful tech teams

What is it like being a female founder in a post-COVID business landscape, trying to raise venture capital while also trying to raise your kids?

Jean Smart is the founder and CEO of Penelope, a venture-backed 401(k) platform that's focused on serving the five million American micro and small businesses. 

Those of us who have worked for a small company will know what a struggle setting up a 401(k) can be. And so, at the height of COVID, Jean gave up her salaried career as a Wall Street exec working in financial services to found Penelope and help folk (like her immigrant parents) invest in their retirement. 

Like most business owners who work for themselves, the '9 to 5' quickly becomes a '6 to 6'. Compromises need to be made about who you spend your time with outside of work and how you break down the goals you are trying to achieve into a manageable maths problem of time best spent. 

There's a self-confidence and self-esteem that Jean exemplifies as she has come into her own as a female founder, unafraid to raise venture capital, make big decisions, not dwell on her mistakes, and create impact with her business. 

This inspiring episode provides valuable insight into the mindset we need to run our own businesses while still running our own lives. Please join us. 

 "If everything's been easy, then starting a company's really hard. But if you've already been doing hard things, then you got this." ~ Jean Smart 

In This Episode:

- What's it like being a female founder?

- What's been the most surprising aspect of the job?

- Learning not to dwell on your mistakes as a business owner

- The advantages of being a female founder

- Jean's advice on how to secure VC funding 

- Reducing your goals to a manageable maths problem

- What are the keys to Jean's success?

And more!

Connect with Jean Smart:

- Website - https://penelope.co/news

- LinkedIn - https://www.linkedin.com/in/jeankimnewyork/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

What is DevSecOps, and how can we embrace it as we continue improving our systems development cycle?

To answer this important question is Sean D. Mack, a transformational technology leader who has literally written the book, ‘The DevSecOps Playbook: Deliver Continuous Security at Speed’.

Appreciating the crucial role that security (at speed!) plays in your DevOps process begins with understanding company culture. It’s not so much about understanding the tools (“moving to the cloud”) as it is about the People, Process, and Technology. 

All the stakeholders need to appreciate that prioritizing security upfront will save time and money in the long run. It’s not a case of security being something too hard to understand so you think that if it’s out of sight, it’s out of mind. 

Ask yourself: what could go wrong if we don’t prioritize security? This is increasingly more prevalent with AI writing code and far fewer eyeballs on the software development process. 

Learning how to begin with the end in mind, ask the right questions, and embrace collaboration are all key issues that Sean helps us to understand. 

Getting things to market faster, better, and now more secure is sure to see DevSecOps gain traction as we learn that it’s not too complex a term to understand. 

How we start employing it in our systems development cycles is something that (thankfully) Sean is giving us some great pointers for, straight from his playbook. Please join us. 

 “One of the things that’s important with dev sec ops (and powerful about it) is that it’s not just about security. It’s about secure at speed.” ~ Sean D. Mack

In This Episode:

• What is DevSecOps? How is it different to DevOps?
• How Sean helps businesses keep their businesses secure (People, Process, and Technology)
• Understanding process: begin with the end in mind
• How important is continuous deployment?
• What are the most costly mistakes of DevSecOps?
• The power of employing a DevOps coach (but not outsourcing the internal change needed)
• Building security into how we work, upfront
• How do non-technical stakeholders think about DevSecOps? 
• How do we educate ourselves about DevSecOps? 

And more!

Connect with Sean D. Mack:

- LinkedIn - https://www.linkedin.com/in/seandmacknyc/

- Twitter - https://twitter.com/SeanDMackNYC

- Sean’s Book - Amazon.com: The DevSecOps Playbook: Deliver Continuous Security at Speed (Audible Audio Edition)

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

What does it take to build a high-performing technology organization? For Nick Maiello, it's a combination of data-driven decision-making, having cross-functional teams, and getting your culture right.

And Nick should know. He has a range of experience, from starting technology companies to scaling out multiple digital transformations in a number of different industries, including consumer travel and e-commerce.

Currently the Co-founder and Chief Technology Officer for Chargely, Nick goes so far as to say that the term 'technology organization' is an outdated one.

We should be 'cutting edge organizations' as we leverage technology and other tools at our disposal to adopt a customer-centric approach to our businesses.

Once you understand your company's 'why', what qualities should you look for when hiring talent to navigate technology's changing landscape? And when it comes to software solutions, do you custom-build or go for off-the-shelf?

Balancing the long-term plan with being iterative, and learning to stay the course with a strong leadership team are more of the ingredients required for a high-performing organization.

Debbie and Nick show that when efficiency is driven by necessity, things start to click. Please join us on this week's impactful episode of Scaling Tech! 

"Embracing P&T (Product and Technology) means embracing a customer-centric approach. Understanding the priorities of the customer comes first and you do this using customer feedback and data analytics." ~ Nick Maiello

In This Episode:

- How can companies embrace the role of Product and Technology in today's digital landscape? 

- How can big-picture thinking benefit software engineering solutions?

- Why is there a need to shift towards custom-built, cutting-edge technologies?

- Understanding 'Build, Borrow, or Buy'

- Why you need passionate people on board for your digital transformation

- Is software eating the world? 

- The importance of being lean and fast in a startup

And more!

Connect with Nick Maiello:

- E-mail - [email protected]

- LinkedIn - https://www.linkedin.com/in/nickmaiello

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

How do we come together and share and learn? And combine that with planning for what we want to do next. Or, to put it another way, how do we take feedback and then actually act on it?

Anthony Coppedge is the principal global Digital Sales Agile Lead at IBM, where he guides the training, facilitation, and coaching of sellers, marketers, product owners, and executive leaders globally across all of IBM in how to apply Business Agility. 

His latest Agile invention is the 'Retrospective Radar', a visualization tool and technique for teams to reflect together in a spirit of continuous improvement. 

It combines Stephen Covey's 'Circles of Control, Influence, and Concern' with 'The Starfish Retrospective' by Pat Kua as the starting point for quantifying qualifiable information and then turning that color-coded feedback into actionable intelligence! 

We've all sat through retrospective meetings where we go over what has and hasn't worked in the past quarter and then tried to work out who does what next. And very often, employees grow tired of giving feedback because nothing seems to change. 

Quite simply, the Retrospective Radar is a more efficient meeting model and work results visualization tool. It combines the Retrospective meeting and Iteration Planning meeting into one team meeting instead of two separate meetings. 

It is undoubtedly a brilliant way for companies to incorporate and act on employee feedback in a way that leads to meaningful company change! 

Anthony's invention and resultant insights prove that communication leads to coordination, which in turn leads to collaboration. 

Company siloes get broken down, time gets saved, and aggregated feedback becomes actionable intelligence. Find out more inside this week's episode of Scaling Tech! 

  "If you can visualize it, you can talk about it." ~ Anthony Coppedge

In This Episode:

- What is IBM's Retrospective Radar?

- The power of being able to pivot from your learnings

- How to quantify a qualifiable problem

- Understanding Circles of Control, Influence, and Concern

- Does feedback lead to change? 

- The Impact of Actionable Intelligence

And more!

Resources:

- About the Retrospective Radar: https://bit.ly/retroradarintro 

- Free MURAL template for the Retrospective Radar: https://bit.ly/muralretroradar

- Creative Commons usage rights for the Retrospective Radar: https://creativecommons.org/licenses/by-sa/4.0/

Connect with Anthony Coppedge:

- LinkedIn - https://www.linkedin.com/in/anthonycoppedge/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

Does process change need to be super complicated? Does change work best when it comes from within a team rather than an external influence? And how can we improve conversations around process change from being less inference-based to more data-driven?

All these questions are raised as we hear 'the chicken story' from Brian Guthrie in today's episode of Scaling Tech, which explores how a synchronistic process can lead to more staff synchronicity, and even engineer empathy!

Brian Guthrie is the CTO and Founder at Orgspace – a people platform for software teams. He's learned to look to improve process through internal change. 

And so while Brian doesn't come in and wave a magic wand and tell teams what to do, he has previously bought a rubber chicken and a bell, and waited while engineers sit on their hands until the next step in the process is ready to be implemented and evaluated. 

'The chicken story' is a neat lesson in being explicit about your goals during process change. Is it okay for staff to wring a rubber chicken's neck while also ringing a bell to say their job is done? Find out in today's insightful episode! Please join us.

"Asynchronicity has a way of hiding slow processes." ~ Brian Guthrie

In This Episode:

- Understanding the goal of engineers being responsible for developing and performing their own merges

- Brian buys his own rubber chicken – and bell!

- How to improve process through internal change

- The need to change the conversation from inference to data-driven

- How to create empathy among your engineers

- What would Brian do differently now? 

- Why process change needn't always be super complex 

And more!

Resources:

- The Chicken Story - https://www.jamesshore.com/v2/blog/2006/continuous-integration-on-a-dollar-a-day

Connect with Brian Guthrie:

- LinkedIn - https://www.linkedin.com/in/bguthrie/

- Twitter - Brian Guthrie (@bguthrie) / X

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

What does transparency in technology look like? What should be hidden, what should not, and what are the expectations?

Today's guest is Josh Tatum, the Co-Founder of Carputty (auto financing, reinvented). Josh has been a driving force in the consumer finance and technology industry for the better part of two decades and brings a wealth of educated opinion and insight to the topic of transparency.

Did you know that supermarkets are using the Bluetooth on your phones to track your in-store movements and then target you with coupons accordingly? Are you aware of what credit reporting agencies are doing with your data when you get into debt with your student loan, or to buy a car?

How do we know that the information we provide tech companies with isn't being sold or used to discriminate against us? And what can we do about the "hyper-targeting" of customers in specific areas and demographic groups?

Josh is giving us plenty to think about as he elucidates on the triangle of Technology, Transparency, and Trust. In his opinion, all people should know what information they are giving away - AND what it is being used for.

As companies are being forced to slow down and consider the consumer's interests more, now is a great time to protect our engineers by being transparent about what we are creating, while still protecting the 'secret sauce' that is our Intellectual Property.

There's an important balance that is worth striving for. Details inside!

"Do consumers really know where credit reporting agencies are gathering their data? Is that transparent enough? You can get your report for free, you can get some things for free, but knowing what they actually do with it would actually scare a lot of consumers." ~ Josh Tatum

In This Episode:

- What does transparency in technology even mean?

- How do we give consumers debt? 

- Can we trust Credit Reporting Agencies?

- Who owns your profile, and who is trusted with your financial information?

- How the auto industry finances your car deal

- What Intellectual Property should be protected from the public?

- How supermarkets use your Bluetooth to track your in-store shopping behavior

- Learning to always ask 'the why?' and to trust your engineers!

And more!

Connect with Josh Tatum:

- LinkedIn - https://www.linkedin.com/in/joshua-tatum-3bb86541/

- Website - https://www.carputty.com/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

How do you tell if you have burnout? Are there key milestones that you should look out for on the way down? And are there healthy indicators to celebrate your recovery? 

Aldric Giacomoni has been a member of the New York Tech scene for over 15 years and is an old friend and colleague of host Debbie Madden. He also suffered recently from burnout, and in today's episode of Scaling Tech, he's candidly sharing what got him through it in a highly relatable episode.

From early warning signs and misdiagnoses, through to the power of having candid conversations with people who know you well enough to point out when something seems amiss, there is almost a methodology of steps and repeatable processes that you can apply as you learn to take care of yourself in the same way as you would your business. 

Discover what helped Aldric tackle the pile of dirty laundry, get back to job hunting, and beat the pandemic blues in this episode of Scaling Tech that seeks to prioritize mental health by starting a conversation. Please join us. 

"I had an outsized emotional response to a question that was not particularly emotionally charged. And that's when I realized: this is probably burnout."  ~ Aldric Giacomoni

In This Episode:

- When do you know that you have burnout?

- What are the misdiagnoses with burnout?

- The importance of having meaningful conversations with people who know you

- Why you should get preemptive professional therapeutic help

- The power of a regular meditation practice

- What are the milestones as you start to recover from burnout?

- Seeing burnout recovery through the lens of repeatable processes

And more!

Connect with Aldric Giacomoni:

- LinkedIn - https://www.linkedin.com/in/trevoke/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

How do you balance technical proficiency with stakeholder goals? Who talks to whom, and who owns the process as you build out your product management teams while showing your stakeholders their much-needed ROI? 

These are some of the challenges Rob Wisniewski has faced over the years as a CTO who has specialized in helping companies scale while automating their big idea. 

Rob Wisniewski is a Managing Director in Blackstone's Technology and Innovations Group and has worked in a variety of tech leadership roles in multiple industries and at various stages of company growth.

Stakeholder sophistication is a key component for Rob as you establish a healthy stakeholder connection while also assessing when to put your product management team in the same room as your stakeholders.

Learning that the stakeholders control the process and that as you scale up your effectiveness as a tech organization, you become more human and therapy-driven anyway (which in turn helps your stakeholder approach) are just some of the smart insights that have made Rob a much sought-after CTO. 

An external valuation can also be important at the right stage of product development as we "learn to get out of the way of our own experiments," as Rob succinctly puts it.

There's also good news in this episode for owners looking to tighten their belts as Rob and Debbie comment on the merits of getting better outcomes with a measure of economic restraint. 

Join us for a lesson in remembering why we create value when we create tech – and how we can protect that process through healthy corporate culture and communication. Please join us. 

"For me, it's about finding that product management discipline, really putting time, effort into your version of it, and making sure that there's transparency with the stakeholders via that function." ~ Rob Wisniewski

In This Episode:

- Appreciating your purpose of creating value with your tech

- Who gets to talk to whom when you're building out your product management?

- Understanding stakeholder sophistication

- Why the process is owned by the stakeholders

- What happens when stakeholder needs and priorities conflict?

- What has Rob seen insofar as 'mistakes in the making'? 

- Getting a better outcome with a measure of economic restraint

And more!

Connect with Rob Wisniewski:

- Website - https://www.blackstone.com/

- LinkedIn - https://www.linkedin.com/in/robwisniewski/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

What are the skills you take when you go from being CTO to head of business operations – and what are the new skills you acquire? And how can a company benefit from having a former CTO looking at its systems and processes? 

Nick Rockwell is currently the EVP for Strategy and Operations at Fastly, having transitioned from within the company as CTO. Before that, Nick was CTO at The New York Times, and he's been a CTO for the better part of 22 years! 

All of this makes him expertly qualified to chat with our host Debbie Madden about the skills an engineering mind can bring to meetings, including how to take a data-informed approach (rather than data-driven) to learning, research, and information, as well as still using data for outcomes. 

The challenges of being cross-functional, learning how to communicate with your teams once senior management has worked out what is a priority, and even the personal identity shift that occurs when you take on a different role within the same company all provide valuable insight into the day to day operations of a thriving tech company. 

The human challenges of team cadence and doing the simple things really well to achieve success are all carefully considered and articulated by an engineering mind who is now re-engineering company systems. 

This episode is for all engineers looking for an insight into what it's like to bring those skills to the boardroom table and take on other company challenges. Please join us.

"It stands to reason that if you want to change anything about how the company runs, it's at least 80% a communications challenge." - Nick Rockwell

In This Episode:

- Nick shares on re-defining his identity within the company 

- Thinking like a product manager – understanding prioritization

- Understanding that every company process is manifested in a system

- Appreciating that the mechanics of corporate communication holds the key to change

- Nick's insights into cross-functionality

- Why a "data-informed" approach is better than a data-driven one

And more!

Connect with Nick Rockwell:

- Website - https://www.fastly.com/

- LinkedIn - https://www.linkedin.com/in/nickrockwell/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

Performance Management! Why is it more important now than ever? And how can you make it a top priority in your organization? In increasingly volatile times, is it worth replacing that person on the team who's giving you 20% less than the next candidate could? And when is a good time to do performance reviews?

Cat Miller is the CTO of Flatiron Health, leading an organization of over 400 technologists who are working together to reimagine the infrastructure of cancer care. Cat is a software and data engineer by training, with over a decade's experience in data-focused startups and nine years growing the team at Flatiron (through acquisition and beyond).

Cat is addressing the issue that most companies either find themselves in a state of hypergrowth or attrition – and in either scenario, there's usually an open headcount.

So, if you're growing fast, there seemingly isn't the time to evaluate performance output. And if there's suddenly a hiring freeze, when someone leaves, you don't receive a backfill for that position. Another challenge is that managers are often not incentivized to performance manage because they don't know what's on the other side of that process.

But as Cat and Debbie concur (and we can attribute the sentiment to Simon Sinek), feedback is a gift. And so thinking about where the person you are evaluating wants to be in five years can help the process.

Good managers care about other people, but it is also about thinking about a person's worth and output from the perspective of the business – and the impact that person's performance has on the rest of their team.

This is a fascinating deep dive into the 'Why, How, What, When, Where, and Who?' challenges that performance management throws up. And if we are looking for steady organizational growth and staff prosperity, these are challenges we need to face. Please join us.

"Product managers really know when their engineering team is delivering – and when it's not." - Cat Miller

In This Episode:

- Why Performance Management isn't a Top Priority (when you have open roles to fill)

- The challenge of performance managing someone out of a role that then needs to be filled

- How can we use business urgency to drive performance? 

- What are the risks of de-prioritizing performance management?

- Who's asking: Is this the best you can do? 

- When is a good time to do performance reviews?

And more!

Resources:

• Burnout: The Secret to Unlocking the Stress Cycle - https://www.amazon.com/Burnout-Secret-Unlocking-Stress-Cycle/dp/198481706X
• Feedback is a Gift - https://www.youtube.com/watch?v=tttv9lRPcLA

Connect with Cat Miller:

- Website - https://flatiron.com/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

What is it like to take seven months and interview literally hundreds of founders and co-founders of businesses before taking your next job as a CTO? 

This is the fascinating story of JP Grace, a seasoned engineering leader who's paved his way in the tech industry with his ability to drive business growth and positive change.

JP Grace is the current CTO of Endear, where he's assisting omnichannel retail brands in driving sales with an easy-to-implement clienteling platform. 

How he got to where he is today is a lesson for aspiring CTOs in being intentional about what they want from their next job – and the lengths they are prepared to go to get it. 

For JP, this involved reaching out to his network, chatting with VCs, and taking countless interviews just to see if that next company could be the right fit. Along the way, he learned how to incorporate interview feedback so that he could tell his story in a more impactful manner.

Learn what chopping wood meant to JP as he figured out how to present his best self and prepare for when the stars aligned with the right career opportunity. 

Your career trajectory can take off too with the intentionality and directionality that JP and host Debbie Madden are astutely discussing in this entertaining episode of Scaling Tech. Please join us!

"You have to spend a couple of hours a week just researching opportunities and understanding 'Is there a business here? What is this company actually doing?'" - JP Grace

In This Episode:

- How JP first got inspired by technology and making new things out of nothing

- What JP learned from interviewing hundreds of business founders over a period of 7 months

- Paying attention to how your message is resonating with the people you're speaking to 

- Learning how to wait for the right opportunity to present itself

- What advice does JP have for aspiring CTOs? 

And more!

Connect with JP Grace:

LinkedIn - https://www.linkedin.com/in/josephpgrace/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

Which is better: onshore versus offshore hiring? This is an important consideration in today's hybrid world. To answer this question, Scaling Tech's Debbie Madden has brought in Joe Burgess: someone who's tried both approaches in recent months.

Joe Burgess started his career as a software developer and teacher at Flatiron School, after which he transitioned into leading teams of data scientists, engineers, designers, and education professionals to build the education product at Flatiron – and then deliver it to tens of thousands of students.

Joe then co-founded Ribbon Education where he now focuses on education and sales. Building startup teams is second nature to Joe, but as he found out with some of his offshore hire experimentation, mistakes can be made. 

This episode is a lesson in, among many things, defining the requirements of the job. Understand those requirements clearly so that a team can communicate at a certain level so that you can attain a certain work level. 

And as simple as it sounds, for Joe hiring early on via Upwork, the ability of his tech hires to understand English proved to be a stumbling block. 

Most startups can ill afford the resources to teach someone the job, and walking that fine line between finding someone who is suitably qualified to build you a CRM platform and giving a young coder an opportunity is well-considered and elucidated by Joe and Debbie. 

How can you go about hiring junior offshore talent? Is timezone important? How do you create the right work culture with a hybrid team? Answers to these questions and more in this week's educational episode of Scaling Tech.

"When you're a brand new startup (and we're just getting going), it's really hard to allocate the resources to teach someone how to do something." - Joe Burgess

In This Episode:

- Joe's early experiences hiring offshore via Upwork

- What are the requirements of the job? Defining those clearly

- The overlap between teaching and management

- The challenges of hiring junior offshore talent

- How to tackle timezone issues

- Understanding your employment law options when hiring offshore

- How to create the right hybrid work culture

And more!

Resources:

- Horsepaste (codenames online) - https://www.horsepaste.com/

Connect with Joe Burgess:

- LinkedIn - https://www.linkedin.com/in/jmburges

- Ribbon Education - https://www.ribbonedu.com/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

How do we think about innovation? And then, how do we scale it? Matt Holford is a Senior Director of Engineering at Etsy and a technology leader who's had quite a storied career working as a musician and in various creative digital service agencies.

As such, he has a unique perspective on how to frame scaling innovation.

How do we give staff the space for idea generation? And then, how do we validate and implement new ideas at a company level? For Matt, opening the door for product innovation means being able to have pockets of creative conversation in high-pressure situations.

It's about having the right expectation of bandwidth to take on new ideas – something that is completely distinct from how good the new idea may be.

Setting goals at the right altitude is also important in today's tough economy. You can set big-level innovation goals that then cascade down to each individual team, but those teams may then feel robbed of the permission to innovate themselves. 

Looking at innovation through the prisms of the individual, the team, and the organization is one of the creative ways that Matt is coming up with new idea-generation methods. Please join us in this fascinating conversation about the cadence and scalability of innovation.  

"The context matters so much in terms of how willing people are to think about technology and engineering as a creative practice." ~ Matt Holford

In This Episode:

- Appreciating how Matt's career has informed his understanding of product development

- How do you take on board engineer ideas while satisfying stakeholder interest?

- Understanding the practice of generating ideas both inside and outside the business 

- How comfortable is Matt with 'throwaway ideas’?

- How do we scale innovation in today's tough economy? 

- Seeing the time required for idea generation as a sliding scale 

- What is the right cadence for idea generation? 

And more!

Resources:

- Ideaflow: The Only Business Metric That Matters - https://www.amazon.com/Ideaflow-Only-Business-Metric-Matters/dp/0593420586

- Creative Strategy Generation - https://www.amazon.com/Creative-Strategy-Generation-Creativity-Strategies/dp/0071850112#customerReviews

- Thinking in Bets - https://www.annieduke.com/books/

- The Voltage Effect - https://www.thevoltageeffect.com/

Connect with Matt Holford:

LinkedIn - https://www.linkedin.com/in/mattholford/?trk=public-profile-join-page

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

How can we be a good partner when we buy from a vendor? How do we, as the customer, get good at providing feedback? As we partner with the right SaaS companies, how do we get the most out of those partnerships right out of the gate? 

On today's episode of Scaling Tech, I am by Ian Lotinsky, a product and team builder who is the CTO at Great Minds, an online ed-tech business. Ian is answering Debbie's questions with his own, such as 'How do we understand the people on the other end of the Zoom call?' and 'How can we learn as much as possible about the people using our products?'

Creating a partnership mindset requires alignment around the question, 'How do we ask questions?' As we embark on a partnership journey, it pays to ask the right questions upfront – at the risk of getting off on the wrong foot. Debbie and Ian delicately unpack this partnership paradox in this intriguing episode. Please join us. 

"One thing I've seen and believe and have read is that you tend to hire culture. And so I've certainly recruited folks and built a team that I could entrust partnerships to." ~ Ian Lotinsky

In This Episode:

- How do you create a partnership mindset?

- How do you get to a positive outcome when you first meet a new vendor? 

- Alignment around the question 'How do you ask questions?'

- ‘Forming, Storming, Norming, Performing’

- Understanding the Theory of Constraints 

- Building trust relationships through empathy

- Upvoting a problem from within the system 

- Building a team based on your values 

- What happens when it comes time to exit the partnership? 

And more!

Resources:

Lead Without Blame - amzn.to/42bMoVs

Connect with Ian Lotinsky:

- Website - https://greatminds.org/

- LinkedIn - https://www.linkedin.com/in/ianlotinsky

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

Who do we look to as we try to implement stage-appropriate processes within our tech company? Is it the Googles and LinkedIns for their HR and staff incentive policies, or is there a better way to 'right size' our process challenges?

Don Neufeld is the VPE Coach (Vice President Engineering), who offers leadership and performance coaching for VPEs, CTOs, and other engineering leaders.

What makes Don so effective is that he's been there as a startup engineering leader himself, from founder to IPO stage – including CTO of Medium and VP Eng. at both ClassPass and Chartboost.

Today Don is offering insight into first understanding your WHY as a small company and not just following in the process footsteps of tech giants. It's about the fine line between being proactive as a tech leader and doing something when it's actually needed.

It’s also about asking if your process is better, worse, or the same as before, and making relative judgments instead of comparing yourself with companies that aren't at the same stage as you. 

What is your 'risk list,' and how are you, as a tech leader, understanding the financial implications of your business as you burn cash to get to market? Growth at all costs may well be undermining your efficiency process, and the new world doesn't look like the old one, so it's important to have a holistic understanding of your business. 

Don's insights may help you solve the right problems for your tech business at the right time – saving you time and money further down the line. Please join us. 

"A stage-appropriate process is the right process for you – not some abstract, correct, best process. Especially in engineering. This can be really challenging because engineers want to do things the right way, and so the idea of having an optimal or best process is very attractive." ~ Don Neufeld

In This Episode:

- How do we define the optimal process for our organization?

- Anticipating the pain points in our processes (without solving the wrong problems)

- Looking at similar-sized companies for policy and process comparables

- What access do you have to a community of your technical peers? 

- How do we know if we've overshot it with our processes? 

- When should you be proactive as a tech leader – and when reactive?

- The value of maintaining a 'risk list' 

- When to reevaluate your processes if you're restructuring or downsizing

- What is the most common mistake startups make?

And more!

Connect with Don Neufeld:

- Website - https://vpecoach.com/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

LLM fluency: what is it, why do tech teams need it, and why should we care about it? LLM transformation is the new digital transformation, and Dan Mason, a principal at Stride Consulting, is today's guest to help us understand all we need to know about Large Language Model transformation.

Dan is a prolific product and engineering team leader who's led teams and products at ESPN, People Magazine, Viacom, and more! Dan has put together a course on LLM fluency and so is uniquely positioned to offer tech leaders out there valuable insight on how they can use deep learning techniques and massively large data sets to understand, summarize, generate, and predict new content. 

It's about understanding the outlines in the beginning so that by becoming a prompt engineer, you can potentially solve some of the more common customer problems you may be grappling with. 

Engaging LLM so you get to the point of initial utility may be a messy, creative process. Still, the upside of having expertise that builds on itself seems well worthwhile for that initial period of experimentation and understanding. 

Because it's all so new and happening so very fast, host Debbie Madden is just about the perfect host when it comes to bringing it back to her audience (tech leaders) and what they can do to increase their LLM fluency for better team productivity.  

Learn more about the downstream effects of unlocking creativity with LLM and more in this thought-provoking new episode.

(on LLM transformation) "Really, what's going on here is just a creative explosion." ~ Dan Mason

In This Episode:

- What is LLM fluency, and how can you use it in your team?

- What should we expect as we embrace LLM transformation?

- Why is LLM the new digital transformation? 

- What new patterns and roles will emerge with LLM transformation?

- How can tech leaders build LLM fluency and capabilities within their teams? 

- How do we engage LLM to get to the point of initial utility?

- What areas of constraint does Dan foresee? 

- The downstream effects of unlocking creativity

- Is the Age of Specialists now over?

- Which industries should be the most concerned?

Resources:

- Stride's LLM Crash "Course":  https://www.stride.build/services/ai-transformation

Connect with Dan Mason:

- Website - https://www.stride.build/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

How do we build systems that improve the way we interact with media and with each other? Truth versus Lies when it comes to content authenticity is today's timely topic and I have brought in Andy Parsons, the Senior Director of the Content Authenticity Initiative at Adobe, to consult!

There is a scientific curiosity for tech leaders around how we discern 'truth' from 'lies' in the media. Especially with the advent of AI, how do we prove what content is false? 

As Andy clarifies, it's actually more beneficial for us to focus on learning what content to trust, rather than proving falsehoods. Given Andy's position at Adobe – besides being a SXSW speaker and oft-quoted tech expert – he's ideally suited to provide insight on the content process that is ‘Capture, Edit, Publish,’ as well as the open source future of Content Authenticity. 

Following on from this is the idea of 'digital provenance' and using metadata that establishes the chain of custody information needed for users to make trust decisions about digital data.

Everyone should have the right to click on a piece of media and know what it is and where it came from. After that, we can make up our own minds about whether it's trustworthy. 

With the good work of the Content Authenticity Initiative, this ideal can become more of a reality as we wade our way through 'fake news' and try to appreciate media content for the honest value it can deliver. Bring on the 2024 US election! 

"It's about trust. And trust is not between computers and cameras. Trust is between humans and organizations." ~ Andy Parsons

In This Episode:

- What does the Content Authenticity Initiative do?

- Understanding the process of ‘Capture, Edit, and Publish’

- What does digital provenance entail?

- Discerning between publishers who need to be verified and authors wanting to remain anonymous 

- How does the Content Authenticity Initiative actually work? 

- How accessible will this technology be? 

- How will we know whether something was generated by AI?

- Can we use AI to detect AI? 

And more!

Resources:

- Content Authenticity Initiative (CAI) Website -  https://contentauthenticity.org/

- CAI Open-Source -  https://opensource.contentauthenticity.org/

- CAI Twitter - https://twitter.com/ContentAuth

- CAI LinkedIn - https://www.linkedin.com/showcase/content-authenticity-initiative/

Connect with Andy Parsons:

- Twitter - https://twitter.com/andyparsons

- Andy Parsons LinkedIn - https://www.linkedin.com/in/andyparsons/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

How do tech leaders learn to lead without blame? Today's guest is Diana Larsen, a truly dynamic and inspirational woman who works with global organizations designing high-performance work systems, and innovating team effectiveness – a theme that is top of mind for most businesses these days. 

We are chatting about the Agile Fluency model, how Diana supports business leaders in their transition to Agile methods, and her latest book ‘Lead Without Blame – Building Resilient Learning Teams.’

All of Diana's books are required reading for anyone wanting to up their Agile game. Her insights into how teams work through the prism of the Agile Fluency model are fascinating, as is her view on how leadership is changing as our technological world is changing. I trust you will enjoy this episode. 

 "It starts with the leaders. Because somebody's gotta at least make that stab in the dark to figure out 'Where are we?... Where do we think we are?... and Where are we really?' ~ Diana Larsen

In This Episode:

- What is the Agile Fluency model?

- Is there a 'target' team for the Agile Fluency model?

- Who decides what level of fluency is for them? 

- What does Diana see happening when a team member is added?

- A success story of a business that has employed Diana's model

- How do you avoid complacency once you've implemented Agile Fluency? 

- How we cultivate more resilient teams - insights from Diana’s new book

And more!

Resources:

- Agile Fluency - http://www.agilefluency.org/

- Diana’s books - https://www.amazon.com/stores/Diana-Larsen/author/B002BM7U7Q?

Connect with Diana Larsen:

- Website - https://www.futureworksconsulting.com/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

How do we visualize systems to improve product development? And where are the bounds of that system? Today I'm chatting with Rob O'Brien about process mapping, value stream mapping, and more. 

Rob is Principal Product Manager at Stride Consulting and has over ten years of product management experience that he brings to this conversation. Rob frames the debate for us by defining the 'socio-technical system' involving people, technology, and processes that all contribute to the overview of how we should see our product development systems.

How do we include the engineers, the finance department, and other organizational leaders to ensure we are creating a system that can improve our products and services and ask the right questions that will ultimately improve the way we do things? 

There's a lot that can go wrong if we make assumptions about which part of our organization needs to be involved in process mapping. Rob shares the value of defining the bounds, asking those 'low-level questions,' and how to structure a two-day conference, say, whereby you are bringing in certain departments at key stages. 

Value stream mapping to improve product development is a favorite topic of mine and one that Rob provides much insight on. I trust you'll enjoy this conversation.

"I think the next biggest one (mistake), that actually feeds to that first mistake, is really thinking about and defining the bounds of what the system is in your world. So what do you mean by 'system' - and getting alignment on that?" ~ Rob O'Brien

In This Episode:

- What do we mean by 'systems visualization?' 

- Where do we get it wrong when we build our product development systems?

- How do we know if we've involved all the relevant stakeholders 'enough'?

- The value of drilling down into some of the 'low-level questions' to ultimately save time

- The importance of having clear definitions so you can go deeper on your processes

- 'If you see something, say something - why it's important to speak up during the process

- Understanding story mapping and other best practice value stream mapping approaches

- How do we understand the specificity of what to capture?

And more!

Connect with Rob O’Brien:

- Website - https://www.stridenyc.com/blog/author/rob-obrien

- LinkedIn - https://www.linkedin.com/in/rob-o-brien-82865b25

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

What comes first: the outcome or the output? Today I'm chatting to Josh Seiden about one of my favorite topics: outcomes over outputs. Josh is actually the author of a book with that exact title, Outcomes over Output: Why customer behavior is the key metric for business success.

Josh is also the co-author of Lean UX: Designing Great Products with Agile Teams, and Sense and Respond: How Successful Organizations Listen to Customers and Create New Products Continuously. 

For Josh, the answer is clear: if we can define an outcome as a change in human behavior that creates value, then it's worth putting that ahead of the output or 'thing' we are creating. 

This is a fascinating approach to redefining the way we work, the way we set OKRs, and the way we measure success. When the name of the game is efficient growth, defining your outcomes is crucial. 

How do we make sure we are committing to the right work, though? And how do we articulate that to the teams that we build? Let's find out!

 "Let's really think about what are the things that people value, what are the outcomes that we're trying to get, and then work backwards to get to the output we need to make."  ~ Josh Seiden

In This Episode:

- Why outputs follow outcome 

- Understanding how outcome is a change in human behavior (that creates value)

- What do we mean when we say "outcome"?

- What do we need to do to deliver an outcome? 

- What are AGILE teams committing to stakeholders?

- How do we think about the way we organize our teams?

And more!

Connect with Josh Seiden:

- Website - https://www.joshuaseiden.com/

- Outcomes Over Output: Why customer behavior is the key metric for business success https://www.amazon.com/Outcomes-Over-Output-customer-behavior/dp/1091173265/

- Sense and Respond: How Successful Organizations Listen to Customers and Create New Products Continuously - https://www.amazon.com/Sense-Respond-Successful-Organizations-Continuously/dp/1633691888

- Lean UX: Applying Lean Principles to Improve User Experience - https://www.amazon.com/Lean-UX-Applying-Principles-Experience/dp/1449311652

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

Mike is the CTO at Greenhouse, the hiring operating system for people-first companies that enables fair and equitable hiring. And today, he's in conversation with me about how to expand customer segmentation after you've hit your product market fit. 

Mike wrote his first lines of code at Greenhouse 11 years ago, and he's continued to grow with the company. There's a lot to learn from Mike as he shares his secrets on learning about different aspects of business and the company (and seeing business learning as a hobby), as well as offering up advice for other startups in the tech space. 

One example is that you don't have to be all things to all people to succeed as a startup in the tech industry. Making decisions that benefit your business and your customer today, and in six months' time, is what you should be concerned with. 

Mike illustratively shares examples of different customers, their different demands, and ultimately how Greenhouse defines their Ideal Customer Profile. I'm sure you'll appreciate this episode of Scaling Tech. Please join me.

"When you start seeing really good retention (and) really good conversion rates, that might be an indicator that you should think about where you have more weakness – and try to get stronger there." ~ Mike Boufford



In This Episode:

- How Greenhouse got its first 200 clients via word of mouth alone

- How does Greenhouse think about customer segmentation?

- How does Greenhouse cater to different customers? 

- Appreciating the lesson of 'stop them at the front door'

- Getting clear about your ICP (Ideal Customer Profile)

- Considering scaling as it pertains to product market fit

- Mike's approach of seeing business as his hobby in order to grow

And more!

Connect with Mike Boufford:

- LinkedIn - https://www.linkedin.com/in/boufford

- Greenhouse - http://www.greenhouse.com

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

Are you part of a tech team that is searching for constant and continuous improvement to get better in your business every quarter, every year, and with every software or product launch? Have you had the term 'OKR' bandied about as you try to decide on your company's Outcomes and Key Results?

Jeff Gothelf is the co-author of Lean UX: Designing Great Products with Agile Teams, and Sense and Respond: How Successful Organizations Listen to Customers and Create New Products Continuously. Jeff is my guest today on Scaling Tech, and he's helping me unpack this popular management concept known as OKRs. 

When should your Key Results be Outcomes driven – and when should they be Output based? How do we give our tech teams the space and autonomy to identify a solution (and the freedom to pivot) while still holding the company accountable to clearly articulated goals?

As well as being a prolific author, Jeff is a keynote speaker, trainer, and coach with large organizations – not only helping them build better products, but also build a culture that builds better products too. As such, he is ideally positioned to offer unique insight into how to create the right OKRs for your company. 

"This is definitely the flavor of the moment when it comes to management ideas." ~ Jeff Gothelf

In This Episode:

- Why 'the making of a thing' doesn't necessarily indicate value delivered to the market

- When is it preferred to set an Outcome-Driven Key Result (over Output)?  

- What do teams often get wrong when setting OKRs? 

- The problem of changing your OKRs just to match the work you're already doing

- The importance of product discovery when setting OKRs 

And more!

Resources:

- Free 1.5-hour Product Strategy Alignment workshop - ideal for any tech teams who seek alignment around ensuring you are building the products/features that are most valuable to your business. Email [email protected] to see if you qualify.

Connect with Jeff Gothelf:

- Sense and Respond: How Successful Organizations Listen to Customers and Create New Products Continuously - https://www.amazon.com/Sense-Respond-Successful-Organizations-Continuously/dp/1633691888

- Lean UX: Applying Lean Principles to Improve User Experience - https://www.amazon.com/Lean-UX-Applying-Principles-Experience/dp/1449311652

- Website - https://jeffgothelf.com/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

Are you a CTO, Chief Product Officer, or Tech leader? Have you been missing all the good things – the passion, the curiosity, the innovation, and the camaraderie – that came from tech conferences since the pandemic took its toll on live events? If so, fear not! I am here to bring the tech industry to your home. 

I'm Debbie Madden, a serial tech entrepreneur and the host of Scaling Tech. Each week I will be interviewing tech leaders as we focus on one key topic, and they share their successes and failures – knowledge that you can then apply to your business and share with your team. 

In this introductory episode, I lay out my plan on how you, as a tech leader, can apply today’s best practices to lead a high-functioning tech team in an ever-changing tech landscape. I'm excited for this journey – let's dive in!

"If we can't bring the tech leaders to the network, we're gonna bring the network to the tech leaders." ~ Debbie Madden

In This Episode:

- Appreciating Debbie's history in the tech industry

- Why Learning is more important NOW than ever for the next generation of tech leaders

- What can we expect from Debbie's new show? 

Resources:

- Free 1.5 hour Product Strategy Alignment workshop - ideal for any tech teams who seek alignment around ensuring you are building the products/features that are most valuable to your business. Email [email protected] to see if you qualify.

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn – https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

Are you a CTO, Chief Product Officer or Tech leader?

Then this one's for you:

If there was one tool that would help you learn best practices and avoid top mistakes so that you can achieve your goals, would you consider that tool?

If you answered "yes," this is the tool you've been looking for.

Debbie Madden is a serial tech entrepreneur.

She is well known for helping teams scale in ways that result in measurable outcomes paired with a strong culture. She is the founder & chair of Stride, a national agile software development consultancy. Stride helps the world's top brands like SeatGeek, Spotify, Codecademy, and Casper get high-quality products to market while modeling the way for tech and product best practices that upskill and enable tech teams.

Episode after episode, you'll hear top tech leaders and experts in their fields sharing first-hand successes, failures, and lessons learned about the topics that are a high priority for today’s tech teams.

Let the technology leaders of our time share first-hand stories of successes, failures, and lessons learned as they lead and grow their teams amid an ever-changing landscape.