In Depth

Todd Jackson is back on the mic to guest host another product-focused episode. This time, he chats with Kesava Kirupa Dinakaran, co-founder and CEO of Luminai, a B2B software tool that helps automate any manual process down to just one click. 

Dinakaran’s personal and professional story is one that you do not want to miss. A former Rubik’s Cube champion and back-to-back Hackathon winner, Dinakaran’s foray into the world of building software products is anything but conventional. The founders stumbled on the idea for its automated “one-click” product started on accident, at a corporate hackathon. 

But it’s exactly this unique worldview and introspective strategies that make Dinakaran’s advice on the path to finding product-market fit for Luminai so fascinating. Formerly called Digital Brain, Luminai is a Series A startup that’s raised nearly $20 million since its launch out of Y Combinator in 2020. 

In this episode, we explore the psychology behind the sales process, why sales leaders should consider pitching straight to the CEO and Dinakaran’s decision to scrap hundreds of lines of written code to focus on building out their most beloved customer feature. 

On the surface, Luminai may seem like just another B2B SaaS startup, but with nearly half the team comprising of former founders (seven of which are ex-YC founders), Luminai is a true example of how the co-founders can really make their mark on shaping their company on the path to product-market fit.  

Our guest today is Douglas Hanna, Chief Operating Officer at Grafana Labs. 

Grafana Labs is an observability stack built around Grafana, a leading open-source technology for dashboards and visualization. Douglas is a seasoned revenue leader, previously leading operations and GTM strategy at Zendesk. At Grafana Labs, Douglas has been instrumental in scaling GTM at the open-source company — building up both team headcount and its revenue model. 

In our conversation today, Douglas dives deep into the process of bringing products to market at an open-source company.

We explore the different facets of building and scaling a revenue model at an open-source company. Douglas opens up the GTM playbook at Grafana Labs sharing: 

You can follow Douglas on Twitter at @douglashanna. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.

Today’s conversation is with Jessica McKellar, co-founder and CTO of Pilot, which is the largest accounting firm for startups. She’s been working on Pilot for the last 6 years with her two co-founders, Waseem Daher and Jeff Arnold. But what makes this founding trio super unique is that they’ve stuck together in not just one, but three different startups. 

As repeat founders, the Pilot team has learned a ton from their first two ventures, K Splice and Zulip, and both netted some positive outcomes. But as Jessica will share today, there were mistakes the team made along the way that prevented both products from becoming an outsized success. 

So she unpacks what they did differently with Pilot — particularly when it came to picking an acute problem and a huge market to tackle. Jessica also shares the tedious process for building the early version of the product, which included looking over Waseem and Jeff’s shoulders as they manually did the bookkeeping for early customers, while she wrote code alongside them. 

Even going back to the earliest days, Pilot had some really strong product-market fit signals, with customers agreeing to pull out their credit card and pay for the product right away when it was just an idea on paper and eventually pulling the Pilot team into expanding their product suite. Make no mistake about it — being a founder is incredibly difficult — but choosing the right problem to tackle can drastically smooth the path ahead of you. 

Our guest today is Artem Kroupenev, VP of Strategy at Augury. 

Augury is a leader in a category they helped to define known as “machine health.” The company sells products that combine hardware, AI, and SaaS within industrial manufacturing. 

Artem joined the team at the very beginning of its journey and helped shape strategies for how the team measured product-market fit, go-to-market, and eventually, a strategy for designing a brand new market category they could compete in. 

In our conversation today, we dive deep into measurable product-market fit and category-creation strategies. Artem shares particular wisdom on:

You can follow Artem on Twitter at @artemkroupenev You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.

Our guest today is Jeanette Mellinger, Head of UX Research at BetterUp and our User Research Expert in Residence at First Round.

In today’s conversation, Jeanette unspools her tested playbook for high-quality customer interviews, with particular advice for founders in the very early days of validating an idea, including: 

You can follow Jeanette on Twitter at @jnetmell 

You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. 

Our guest today is Claire Hughes Johnson, former COO of Stripe and author of the new book, “Scaling People: Tactics for Management and Company Building.” 

Claire joined Stripe as its COO back in 2014 and, over the course of her nearly seven years in the company’s executive suite, she oversaw rapid growth as Stripe scaled from under 200 employees to over 7,000. Prior to Stripe, she spent 10 years at Google leading various high-impact business teams. 

In today’s conversation, In today’s conversation, Claire takes us behind the scenes at some of the most pivotal moments in her life that turned her into the type of leader she is today, including:

You can follow Claire on Twitter at @chughesjohnson. Check out her new book, “Scaling People,” as well as the book she recommended from Fred Kofman titled “Conscious Business.”

You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.

Our guest today is Rachel Hepworth, Head of Marketing at Notion. 

Rachel currently runs growth marketing at Notion, and sees her job as bringing process and control to all of Notion’s different marketing channels. Before joining Notion, Rachel launched the first growth marketing team at Slack, laying down the tracks for a well-oiled go-to-market strategy that could be measured easily. 

Much like Slack, Notion has made a name for itself largely through customer love and a powerful word-of-mouth recommendation engine. As a metrics-focused marketer, Rachel opens up her playbook on how she lassos that kind of word-of-mouth growth and the analytical approach she has toward acquiring and retaining customers. 

In our conversation today, we focus on the nuts and bolts of what growth marketing looks like inside an organization that’s driven by product-led growth. Rachel shares tactical advice on:

You can follow Rachel on Twitter at @rachelhepworth. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. 

Our guest today is Nadia Singer, Chief People Officer at Figma. 

Nadia joined Figma in 2020 and has seen explosive growth in her own career alongside the collaborative design platform’s. Before Figma, Singer was a talent expert who has hired hundreds of talented folks at places like Quora, Facebook and Google. 

In our conversation today, we dive deep into what makes someone a terrific talent evaluator. Nadia opens up her own recruiter playbook and shares:

You can follow Nadia on Twitter at @nadsinger. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. 

Todd Jackson is back on the mic to guest host another product-focused episode this week with Christina Cacioppo, the co-founder and CEO of Vanta. 

Vanta is the leading automated security and compliance platform, with thousands of businesses relying on the product to get compliant (and to stay that way).  

After toying with some initial ideas, like a voice assistant for biologists, Christina started building Vanta to solve a problem that didn’t really exist at the time. The company started out in 2018 by trying to get SOC-2 security compliance for startups — but at the time, startups didn’t even really need to have SOC-2s. 

But Christina and her team saw the writing on the wall and that security was going to shoot up on the priority list for even the earliest-stage companies, and kept building even when plenty of smart people told them it was a bad idea.

It’s a gamble that paid off. After going through Y Combinator, the team nabbed some truly incredible early customers, including Segment, Front and Lattice. Christina tells us exactly how she went from zero selling experience to pulling off big-time deals. 

She also pulls back the curtain on some of Vanta’s more unconventional moves, like waiting until they acquired hundreds of customers to build a proper website and instead relying almost exclusively on word-of-mouth to grow the business. Christina also shares her thinking behind the fundraising strategy, in which Vanta operated at cash flow break-even for years before going out to raise its Series A. 

Our guest today is Ben Lang, Head of Community at Notion. 

Since joining the company in 2019, Ben has had his hand in several high-impact projects at Notion that has grown its tight-knit community of passionate Notion evangelists into millions of users today. 

But before he was doing this as a full-time job, Ben was already spreading his love for Notion in his free time as a voracious product user. After discovering the tool on Product Hunt, he became obsessed. He got on the company’s radar after launching his own Notion template gallery on Product Hunt and joined as one of the first 15 employees. 

In our conversation today, we focus on the nuts and bolts of building a global community that drives user growth. Ben shares tactical advice on:

You can follow Ben on Twitter at @benln. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.