Scaling Tech - The Blueprint for Successful Tech Teams

Latest Episodes:

Building a Tech Stack For Your Startup with Heman Duraiswamy Jan 16, 2024

Show notes

How do you build your tech stack so that your underlying systems are strong enough when you scale? Today's guest has 20 years of experience building scalable and robust technology stacks for companies across the board – he’s ideally suited to answer that question.

Heman Duraiswamy is the Co-Founder and Chief Technology Officer of Circa, building stronger communities through payment innovation. In a nutshell, his company is revolutionizing the rent collection process in the multi-family real estate industry.

Heman shares his experience transitioning from working for a multi-billion dollar enterprise to starting his own business, and the challenges and differences he faced in building a tech stack for a big company versus a startup.

He also talks about the importance of product-market fit, the factors to consider as a technical founder, and the role of monitoring and iterating in the success of a startup.

If you're looking to make sure that your tech stack isn't a liability as you 10X and scale, this one's for you!

"The single most important thing (as a technical founder) that you cannot compromise is making sure that you're building your architecture, your underlying systems... that are scalable." ~ Heman Duraiswamy

In This Episode:

- How Heman transitioned into starting his own business

- The key ingredients needed to be a successful technical founder

- How Circa payments work in helping with rent cashflow

- How to hedge against your tech stack liability

- The importance of proper monitoring (correlation IDs)

- It's not what you build, it's how you build it

And more!

Connect with Heman Duraiswamy:

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

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

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 It's Like To Be A Female Founder with Jean Smart Jan 02, 2024

Show notes

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/

The DevSecOps Playbook: Deliver Continuous Security at Speed with Sean D. Mack Dec 19, 2023

Show notes

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/

Building a High-Performing Product and Technology Organization with Nick Maiello Dec 05, 2023

Show notes

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 - nickmaiello@chargely.app

- 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/

IBM's Retrospective Radar with Anthony Coppedge Nov 21, 2023

Show notes

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/

The Chicken Story with Brian Guthrie Nov 07, 2023

Show notes

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/

Transparency in Technology with Josh Tatum Oct 24, 2023

Show notes

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 To Beat Burnout with Aldric Giacomoni Oct 10, 2023

Show notes

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/

Balancing Tech Proficiency and Stakeholder Goals with Blackstone's Rob Wisniewski Sep 26, 2023

Show notes

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/

Going from CTO to Business Operations with Nick Rockwell at Fastly Sep 12, 2023

Show notes

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: