Jan 15, 2021 · 50m · saastr
How To Collaborate, Manage & Work With Developers With Jeff Lawson, CEO Twilio
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this SaaStr session, Twilio founder and CEO Jeff Lawson joins Jason Lemkin to discuss his book 'Ask Your Developer,' outlining how business leaders can bridge cultural divides with engineering teams, organize around customer problems, and leverage modern API platforms to drive digital innovation.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Jason holds 17.5% of the talking time here. How this is scored →
Jason as informed peer 4.2 Guest teaching 4.9 Guest disagreement 1.7 Jason pushing back 2.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 22:23 Rejecting the unexciting work framing
Jeff directly counters Jason's premise about getting engineers to work on 'less exciting' tasks, warning that framing work as uninspiring guarantees leadership failure.
Hardest push from Jason ▶ 35:37 Challenging API experimentation against enterprise realityJason pushes back against the friction-free experimentation narrative by pointing out that enterprise change management and core stack replacements only happen once a decade.
Biggest teaching moment ▶ 3:30 Explaining why adding budget delays late softwareJeff educates business leaders on the counterintuitive reality of Brooks's Law, explaining why throwing more money and people at late projects causes further delays.
Jason holds their own ▶ 46:36 Citing transatlantic investment portfolio operational realitiesJason draws on his direct experience managing and investing in five US-Paris SaaS companies to challenge Jeff's strict three-time-zone operating rule.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Bridging the Gap Between Business Leaders and Software Developers | 4 | 4 | 1 | 1 | Jason sets up the premise of business leaders struggling to manage software engineers. Jeff agrees and elaborates on counterintuitive software dynamics, such as why adding budget to a late project delays it further. | |
| The Shift to Digital Customer Interfaces: Build Versus Die | 3 | 5 | 2 | 1 | Jeff explains the paradigm shift from outsourcing IT to 'build versus die', illustrating how digital interfaces define modern customer experience. Jason chimes in with agreement and an illustrative banking anecdote. | |
| Two-Pizza Teams and Sharing Problems Rather Than Solutions | 4 | 5 | 2 | 3 | Jason pushes Jeff on whether Amazon's two-pizza team concept can scale in companies that cannot attract top-tier engineering talent. Jeff explains that small teams succeed by focusing on customer problems rather than relying on 10x talent. | |
| Breaking Down Silos to Connect Developers Directly with Customers | 4 | 3 | 1 | 1 | Jeff discusses breaking down organizational silos by having engineers do customer support and join sales calls. Jason strongly agrees and suggests a cadence of once per quarter. | |
| Recruiting Engineering Talent and the Power of Executive Involvement | 4 | 5 | 1 | 2 | Jeff describes recruiting strategy against big tech monopolies and recounts how executive involvement persuaded leaders at Domino's and the US Digital Service. Jason validates the Domino's transformation thesis. | |
| Inspiring Ownership and Balancing Inventors with Maintainers | 4 | 6 | 3 | 2 | Jason asks how leaders can motivate developers to handle unglamorous tasks like refactoring and bug fixing. Jeff reframes the premise, arguing that treating it as unexciting guarantees failure and explaining the distinction between inventors and maintainers. | |
| The Interplay Between Product Leadership and Engineering Teams | 4 | 5 | 2 | 2 | Jason asks how to balance the role of product management and engineering without turning devs into mere task executors. Jeff explains that product management's role is to direct resources and connect engineers with real user context, sharing a Bloomberg terminal case study. | |
| The API Economy and Lowering the Cost of Innovation | 5 | 5 | 1 | 1 | Jason cites Fastly's enterprise buyer data to ask about developer purchasing power in low-code/API ecosystems. Jeff outlines the transition to digital supply chains and explains how micro-cost experimentation drives innovation. | |
| Investing in Developer Platforms and Safe Experimentation | 5 | 6 | 2 | 4 | Jason challenges whether enterprise business process change management can actually keep pace with rapid developer experimentation. Jeff counters by outlining internal platform investments and lightweight sandboxed prototyping strategies. | |
| Adapting to Distributed Teams and Company Operating Models | 4 | 5 | 2 | 2 | Jason asks Jeff to address distributed hiring across global regions post-pandemic. Jeff advocates investing locally while establishing clear team operating systems bounded within three time zones. | |
| Structuring Distributed Executive Teams and Time Zone Management | 5 | 5 | 2 | 3 | Jason pushes on the three-time-zone constraint using his experience with transatlantic portfolio companies. Jeff clarifies why executive teams can be distributed while individual execution teams need timezone proximity to maintain informal communication. |
Statements from this episode (14)
Lawson: Adding money or people to a late project delays it further
“You can't just throw more money or people at a late project and expect it to catch up. In fact, if anything, that will make it further delayed.”
Lawson: Customer interfaces are digital, making software development a core differentiator, not outsourceable
“The interface that most businesses have with their customers has become a digital interface... And so in that world, IT is no longer something to be outsourced. It is the source of competitive differentiation in the eyes of your customers.”
Lawson: Tech strategy shifted from 'build versus buy' to 'build versus die'
“It used to be in the old world of IT, you had these classic build versus buy decisions. Are we going to build something? Are we going to buy it? Right? And now it's become build versus die. Because if you aren't building software that answers your customers ne…”
Lawson: Small teams of under 10 are a company's engine of progress
“The engine of progress inside of a company is a small team, less than 10 people, who are focused on a particular customer and a particular customer problem, and those define the mission of that team, as well as the metrics of their success in solving that prob…”
Lawson: Companies should give developers problems to solve, not spec sheets
“You should share problems, not solutions with developers.”
Lawson: Twilio requires engineers to work support shifts two days a year
“There have been times at Twilio where we have all of our engineers take turns doing support, you know, like two days a year.”
Lawson: Relying on 10x engineers is not a viable corporate strategy
“It's not a strategy to say, I'm only going to hire these like, you know, top one percent, you know, 10 X developers, and that's how I'm going to build my company. The strategy is how do I take a wide variety of engineers and make them work together as a team t…”
Lawson: Domino's stock outperformed Google, Amazon, and Facebook over the past decade
“The Domino's stock since in the last decade has outperformed like Google and Amazon and like Facebook.”
Lawson: Instilling customer ownership motivates developers to do mundane maintenance work
“Instilling that sense of ownership, I think, is how you actually get everybody to care about even, you know, the more mundane parts of whatever someone's job is.”
Lawson: Engineering teams require distinct developer archetypes of inventors and maintainers
“And the same thing goes for developers. You've got the developers are really good at forging the new thing and inventing the new thing, and they can write a ton of code in one afternoon that you know, invents a new product. And there's other developers who are…”
Lawson: Product leaders should connect developers directly to customer problems
“I think the product leader's job is to try to direct the effort, and instead of prevent developers from, like, having to interact with customers, is facilitating the understanding of the customer for the rest of the team.”
Lawson: Top software companies spend 40% to 50% of R&D on internal platforms
“It's not at all uncommon for great software companies to spend upwards of 40, even 50% of their total R&D budget on those platforms. Because those investments are multiplying the investments that you're making in the other 50% of your R&D investments.”
Lawson: Distributed teams should stay within three time zones for workday overlap
“My recommendation, keep them within three time zones of each other. So you've got a maximum amount of overlap in the workday so that they can collaborate effectively.”
Lawson: Twilio employees will shuffle teams based on remote work preferences post-pandemic
“Within Twilio, I suspect when we can go back to offices, there will be a bit of a team shuffling going on, because certain teams will say, we want to be back in an office, and other teams will say, we're really happy virtual, and people will find the teams tha…”