Short Byte: Lee Edwards - How to pick the right tech startup Whether you’re thinking of founding, joining or investing in an early stage tech company, Lee Edwards has some advice! From effective due diligence on an early stage company to some interesting focus areas for deep tech startups. Lee is a partner at Root Ventures - a hard tech seed VC, and was previously CTO/VPE at Teespring and an Engineering Manager at Groupon. Special thanks to our global partner – Amazon Web Services (AWS). AWS off...
Feb 20, 2021•33 min•Ep. 114
Short Byte: Johnny Ray Austin - Measuring outcomes vs. inputs How can you best measure the effectiveness of your engineering team? Lines of Code written? Number of PR’s? There are absolutely some input metrics that can have some value, but we don’t hire engineers to write code, we hire them to solve business problems. In this discussion Johnny Ray Austin, CTO at Till shares his experiences of managing his org by focusing on the outcomes produced rather than the inputs delivered. Special thanks t...
Feb 13, 2021•30 min•Ep. 113
Building vs buying software Building vs buying is always a fraught decision. Nominally buying a solution provides more capability and a quicker time to market, but then you have the potential of vendor lock in and being constrained by the limitations of the tool that you chose. And in the engineering world, it’s even harder. While Not Invented Here syndrome is becoming less prevalent, you still need to pick between a ground up implementation or leveraging open source, professional open source an...
Feb 06, 2021•28 min•Ep. 112
Building a startup within a startup There are a unique set of constraints when you’re running an engineering team at a “startup within a startup” - from managing the planning cycle before you’ve hit product market fit, to customizing elements of your product and infrastructure designed for a very different audience. Join us to hear how Heidi Williams , Director of Engineering at Grammarly is working on these challenges by building out an enterprise offering for a traditionally consumer focused b...
Jan 29, 2021•29 min•Ep. 111
JP learned engineering management the hard way - and he’s passionate about helping new engineering leaders to have a better pathway to building their skills. In this Short Byte we look at the differences between being an engineering leader at a startup vs a larger company, how JP learned to become a manager, resources that are now available for engineering leaders and some hints and tips on managing your boss and hiring effectively at a startup. Special thanks to our global partner – Amazon Web ...
Dec 17, 2020•29 min•Ep. 110
Culture work is part of a developers job At Flatiron Health, the team thinks that getting IC’s to invest in the team culture is so important that they’ve built it into their career ladder. So I’ll be asking Cat why “culture work” (from onboarding and mentoring to planning hackathons and running socials) is everyone’s job and how it has helped her to build a cohesive and inclusive culture despite explosive growth of her engineering org. Special thanks to our global partner – Amazon Web Services (...
Dec 03, 2020•28 min•Ep. 109
According to Christian Beedgen CTO and co-founder of Sumo Logic, there is no magic bullet when it comes to innovation. His brain child, Sumo Logic, was founded to empower digital business through real-time analytics delivered as a service. On this week’s episode of CTO Connection, Christian and Peter chat about the future of log files and where machine learning fits in. Christian also discusses his long road toward becoming a founder and CTO. Take a listen to the episode. (01:11) - Falling forwa...
Dec 02, 2020•37 min•Ep. 108
Companies have largely figured out software. Data science, however, seems to be the new frontier. Many data scientists are coming from largely academic backgrounds and maybe don’t understand how to function at jobs in the private sector. Today’s guest is Ian Wong , co-founder and CTO of Opendoor. He chatted with Peter about the questions data scientists can ask themselves to better align their work with tangible business outcomes. Ian also discussed how the pandemic has led his team to talk abou...
Oct 08, 2020•44 min•Ep. 107
Content should be both structure driven, and easily integrate with software. But most Content Management Systems are legacy systems that are not intuitive and clunky. Paolo Negri , co-founder and CTO of Contentful , was an early adopter of GraphQL. This week on CTO Connection, Paolo talked to Peter about why GraphQL works so well for content and why organizations should strive to be API-driven. Tune in for his thoughts on management. (01:12) - Paolo's journey to building an org (04:42) - Life wi...
Oct 01, 2020•36 min•Ep. 106
Thanks to the pandemic, many people are getting their first taste of working remotely. But for Gustavo Niemeyer of Canonical, having a globally distributed team is just a way of life. On this week’s episode of CTO Connection, he discusses the pros, cons, and considerations for companies considering globally distributed teams. Further, Gustavo talks to Peter about managing teams looking to solve big, open-ended problems, why finding motivated employees is key, and why he is a proponent of globall...
Sep 24, 2020•42 min•Ep. 105
Sites like Squarespace and Shopify have simplified the design and engineering process for people who either don’t have the technical skills or the resources to hire a team of engineers. However, there is no one-size-fits-all approach for the tools a business will need. Julien Lemoine is the co-founder and CTO of Algolia, a hosted search platform. He joined Peter for a discussion on API and customization. Listen as Julien discusses why things are trending toward customization and greater flexibil...
Sep 17, 2020•38 min•Ep. 104
When Justin Dean was placed as a network engineer in the Marine Corps, he had no idea that this would lead to a career helping legacy and emerging businesses shape what is possible in network engineering. Justin is currently the CTO and CIO of Weedmaps, a website that helps customers find local weed dispensaries and helps dispensaries stay in compliance with state regulations. Today, Justin takes us through his jobs at Shopzilla and Ticketmaster before arriving at the industry changing Weedmaps....
Sep 10, 2020•54 min•Ep. 103
Rob De Feo has spoken to more than 500 startups over the last few years in his role as a startup advocate. These experiences have given him insider knowledge on the patterns leaders in startups face as well as best practices that have helped businesses reach scale. This week on CTO Connection, Rob takes Peter behind the curtain of life as a startup advocate. They also discuss their biggest career advice: searching for roles based on tasks rather than titles. Tune in for Rob’s insights. (01:10) -...
Sep 03, 2020•40 min•Ep. 102
If you’re a startup or any company that doesn’t have vast name recognition, attracting top talent can be a key concern. Ashish Aggarwal cut his teeth at Microsoft, Amazon, and Postmates so when the time came to start his own company, Productiv, he knew how to get the right people for the job. Ashish spoke candidly about his past experiences and how they have helped shape Productiv. He shared with Peter the two things that attract top talent: challenging problems to solve and the opportunity to w...
Aug 27, 2020•40 min•Ep. 101
According to Raj Sethuraman , good technology cannot be a successful technology unless it solves customer problems and drives great business outcomes. Raj is currently CTO at Wolters Kluwer and got his start at Intuit. The common thread throughout his career has been establishing customer-centricity to better inform technical decisions. He is our guest this week on CTO Connection and talked to Peter about a program he likes called “Follow Me Home” in which he and other team members sit down with...
Aug 20, 2020•37 min•Ep. 100
Greg Thomas is the author of the book, Code Your Way Up . Over the course of his 20 years in software development, he found that there was a void when it comes to developing individuals on a team into leadership and management roles. Greg joined Peter to talk about some of the most important principles discussed in his book. He discusses why feedback isn’t always a pat on the back and shares three questions you should be asking when you join or build a new team. Listen for his advice. (01:32) - ...
Aug 13, 2020•36 min•Ep. 99
In any industry, communication is a key factor in a team’s success. For CTOs navigating complex problems, effective communication between all stakeholders is paramount. David Subar is both a Chief Product Officer and Chief Technology Officer at Interna Consulting. He joined Peter to discuss common patterns that result in communication breakdowns. David shares some of the clashes that can happen when a CEO’s vision is not in alignment with the metrics or working style of the team. He also discuss...
Aug 06, 2020•35 min•Ep. 98
Fleming Shi has been with Barracuda Networks for more than 15 years. In that time, there has been a profound shift and evolution in the tools and security systems that power his engineering team. He joined Peter for this week’s edition of CTO Connection to discuss his journey to CTO as well as the many changes he’s witnessed over the years. Listen for Fleming’s thoughts on keeping up with trends as well as the character traits of 10xer engineers. (01:27) - Fleming's career journey (04:17) - Movi...
Jul 30, 2020•33 min•Ep. 97
Data science has increasingly become an integral part of the technical makeup of organizations. However, most CTOs don’t have experience building a data science component from scratch. Jon Morra got his start in data science at eHarmony when most technical teams did not have any researchers. He joins Peter today on CTO Connection to offer advice on how to build a research team from the ground up. Jon discusses why you want to bring on researchers who are generalists and why it is imperative that...
Jul 23, 2020•36 min•Ep. 96
VP of Engineering is an expansive position. But what is it really like on the granular level? Alexandra Paredes is the VP of Engineering at Code Climate and joined Peter to discuss how she approaches the hiring process, keeps her team on track, and navigates metrics such as cycle time and code review involvement. Tune in to hear Alexandra’s thoughts on communication and transparency as well as mentoring new engineers to ensure they ask the right questions from the start. [01:28] - Alexandra's ri...
Jul 16, 2020•33 min•Ep. 95
Working nonstop without delegating is not a sustainable way to live or work. Such habits often lead to burnout. CTOs in particular struggle with this problem. Many are young, inexperienced, or desirous of being part of a shippable product to relinquish control. Andy Skipper was once such a CTO himself. Now he coaches and mentors other CTOs with his company, CTO Craft. Andy joined Peter for this week’s episode of CTO Connection to discuss what burnout is, how to identify it, and what tools you ca...
Jul 09, 2020•36 min•Ep. 94
According to James Smith , CEO of Bugsnag, caring about customer experience is what makes for a better software developer. This is especially important when managing technical debt. Today on CTO Connection, James shares his experience and discusses his approach toward technical debt from both the developer and client perspectives. James shares why he believes overcommunication is key and how carving out time can help your team achieve a manageable sprint cadence. Listen for more. [01:26] - Becom...
Jul 02, 2020•42 min•Ep. 93
Let’s say you join a new organization. How would you spend your first hundred days if you were to figure out how to enact change and implement your own priorities? Our guest this week on CTO Connection is Andrew Fawcett , CTO of Avantica. Andrew has worked with companies of all sizes and has seen some truly amazing changes made, but also has run into those that lacked vision. Andrew sat down with Peter to discuss some of the reasons why companies have such a hard time with change as well as best...
Jun 25, 2020•34 min•Ep. 92
We all want our companies to succeed so it’s easy to get fixated on numbers that we believe will help us judge our efforts. However, according to Dalia Havens of Netlify, metrics need to be optimized to give you a full picture of company or project health. Today, Dalia talks to Peter about using metrics in a healthy way that can empower and help solve problems. She also discusses why a consistent delivery pattern will give you the most insight into your operation. Listen to her thoughts. [01:26]...
Jun 18, 2020•33 min•Ep. 91
When we think of startups we think of charismatic entrepreneurs plugging away on their passions. But what does it really take to form a startup? Our guest this week on CTO Connection is Bob Friday , CTO of Mist, a Juniper Company. Bob is a veteran who has been through the startup process many times. He talked to Peter about the thought processes that go into crafting both teams and entire organizations. Bob also talks about the formula behind the process new ventures will go through and which po...
Jun 11, 2020•37 min•Ep. 90
When companies transition from private to IPO, there are bound to be challenges and learning curves. Rachana Kumar has worked in five countries, two of her positions were in the non-profit sector. These experiences helped her roll with the punches as her current employer, Etsy, has undergone a massive change over the last few years. Rachana is preparing for a talk on helping leaders navigate large organizational changes. In this week’s episode, she explains to Peter the three foundational tools ...
May 28, 2020•38 min•Ep. 89
Learning doesn’t end once you’ve earned your degree. Developers and engineers must stay up to date with their skills and emerging technologies. But most of the time, employees are expected to take on this additional learning on their own. Our guest this week on CTO Connection is Kwame Thomison , a consultant and leadership coach formerly of Meebo, Facebook, and Asana. Kwame discusses different learning models that can be integrated into workplaces to create a strong culture of learning and colla...
May 21, 2020•34 min•Ep. 88
When COVID-19 hit, UserTesting was already at a unique advantage: the team was already mostly working remotely. However, as the stay at home orders have increased, UserTesting’s CTO Kaj van de Loo has seen some unforeseen issues pop up. This week on CTO Connection, we’re discussing how the pandemic has not only changed the structure of work, but also the expectations people have of working in an office. Kaj discusses why everything (no matter how small) must be documented, why managers need to p...
May 14, 2020•36 min•Ep. 87
Kunal Anand has an interesting background for a CTO. Despite majoring in business, Kunal got his start at JPL (an offshoot of NASA). From there he worked at Myspace and the BBC. His experiences at each of these companies taught him invaluable lessons that led to him founding his own company which was acquired by Imperva where he currently serves as CTO. Peter talked to Kunal about his diverse resume and then pivoted to an insightful conversation on the future of work. Kunal offers invaluable tip...
May 07, 2020•48 min•Ep. 86
Hypergrowth is what every startup dreams of, but actually filling the seemingly unlimited positions available is incredibly taxing on employees. Cat Miller is the Vice President at Flatiron Health . At one point, she took on the enormous burden of interviewing at least four people a week. Recognizing the strain on resources, she and her team set out to streamline their hiring process. Today, Cat is sharing what she’s learned from her year of panic in which she hired 100 engineers, as well as how...
Apr 30, 2020•32 min•Ep. 85
