Aug 23, 2017 · 28m · saastr
Zendesk From Day 0 to Today: The Lessons Learned
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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 fireside chat, Zendesk CEO Mikkel Svane and venture capitalist Devdutt Yellurkar explore the key milestones, operational lessons, and strategic pivots required to scale Zendesk from a nascent Danish startup into a public SaaS powerhouse. Svane provides actionable insights on navigating economic downturns, evolving go-to-market models, and maintaining founder humility across each stage of revenue growth.
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 0.2% of the talking time here. How this is scored →
Jason as informed peer 3.5 Guest teaching 1.6 Guest disagreement 0.8 Jason pushing back 0.1
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 23:55 Rebutting the Outside Sales Premise
Mikkel gently rejects Devdutt's framing of Zendesk building a traditional outbound sales team, insisting their model remains land-and-expand.
Hardest push from Jason ▶ 22:02 Devdutt Drilling on Market SegmentationDevdutt presses Mikkel on how Zendesk managed to move from a single flat $9 tier to multi-tier enterprise pricing.
Biggest teaching moment ▶ 18:15 Masterclass on SaaS Pricing TraumaMikkel provides an unvarnished lesson on how abruptly hiking prices alienated customers and taught the executive team that subscriber trust is paramount.
Jason holds their own ▶ 25:02 Contextualizing the 2014 IPO LogjamDevdutt demonstrates his venture background by contextualizing the frozen 2014 IPO market and Zendesk's pioneer role in reopening public tech offerings.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Welcome, Introductions, and Zendesk Company Overview | 2 | 0 | 0 | 0 | Devdutt opens with brief introductory banter, polling the audience about early investor Christoph Janz before asking Mikkel for an overview of Zendesk. The atmosphere is warm, friendly, and entirely collaborative. | |
| Earnings Success and the Early Founder Mindset | 3 | 1 | 1 | 0 | Devdutt brings up 2008 founding emails to probe when Zendesk knew it could be big. Mikkel dismisses the idea of ever feeling like they have 'made it,' comparing startup life to cycling up endless mountains in the Tour de France. | |
| Scaling Zero to $1M ARR and Angel Support | 4 | 2 | 1 | 0 | Devdutt provides context on early venture dynamics while Mikkel details the 18 months it took to reach $1M ARR in Copenhagen. Mikkel candidly shares how vital early angel Christoph Janz was in educating them and preventing common toxic angel behavior. | |
| Navigating the 2008 Crash and Moving to SF | 3 | 1 | 1 | 0 | Devdutt brings up the 2008 'RIP Good Times' crash, prompting Mikkel to describe the agonizing experience of ghosted VC term sheets and moving young families from Denmark to San Francisco. | |
| UX Innovation, Early VCs, and Brand Strategy | 4 | 2 | 1 | 0 | Devdutt and Mikkel discuss how Zendesk pioneered consumer-grade UX in B2B software and built a brand centered on tranquility to counter the stress of customer support. The tone remains collaborative with shared venture history. | |
| Scaling $1M to $10M ARR and Pricing Lessons | 4 | 3 | 1 | 0 | Devdutt prompts Mikkel about early trauma, leading to Mikkel's story about disastrous price hikes that sparked a customer revolt. Mikkel explains how the resulting backlash taught them hard lessons on customer trust, even prompting them to print vulgar customer complaints on company t-shirts. | |
| Scaling $10M to $100M ARR and Adding Sales | 4 | 2 | 1 | 1 | Devdutt asks whether self-service remains core and probes into enterprise outside sales. Mikkel clarifies their land-and-expand approach rather than standard outbound enterprise sales, explaining how they transitioned from pure inbound self-service to assisting larger accounts. | |
| The 2014 IPO and Long-Term Execution | 4 | 2 | 0 | 0 | Devdutt highlights Zendesk breaking the 2014 tech IPO logjam and setting a $1B ARR goal by 2020. Mikkel explains why IPO valuation matters less than setting up post-IPO market trajectory and execution. |
Statements from this episode (10)
Svane: Zendesk has close to 100,000 business customers globally
“Been on this journey for almost 10 years now and have close to a 100,000 businesses around the world using our software for providing great customer service, great customer engagement.”
Yellurkar: Zendesk generated $312M in revenue in 2016
“Three hundred and twelve million dollars in revenue in 2016, that's about three hundred and twelve million dollars more Than when Kristoff and I met you.”
Svane: Bad angel investors ruin early startups with personal agendas
“I see so many examples with small startups, where, you know, they get ruined by early angel investors, who are, you know, spending all their time challenging the company, and like, have their own agendas, and like, don't focus on just making the founder great,…”
Svane: Zendesk Scaled From $0 to $10M ARR in 36 Months
“Zero to one took us 18 months, and one to 10 took us another 18 months, so of course it was a very, very busy 18 months”
Svane: Zendesk operated with no sales team until $10M run rate
“Until, kind of, our first, you know, until, like, ten million dollars in, in run rate, we didn't have sales. It was all a self-service business.”
Svane: Flexible pricing and packaging is competitively disruptive
“Being really flexible with your pricing and your packaging can be really, really competitively disruptive. That you can come with a price point, or you can come with a pricing model that works for your customer, that is almost, that feels designed for their ne…”
Svane: Zendesk expanded from small UK division to thousands of Adobe users
“Our first Adobe customer was a small division in the UK, and now we have, you know, thousands of people within Adobe using our software. Same with Disney and a lot of other organizations”
Yellurkar: Zendesk broke the 2014 tech IPO logjam
“In 2014 there was a log jam, right? Nobody wanted to take the companies public. Like, there was a big, and you were, actually, you were the jam cracker. You broke that log jam and were the first company to get out.”
Svane: Fundraising is about future positioning, not valuation
“What matters is that you grow up, you get out there, and I think for any kind of fundraising, it's ultimately not about the valuation. It's really about the team and the path you set yourself up for after that.”
Svane: B2B startups can disrupt legacy vendors via consumer-oriented CIOs
“Everybody here who has a B to B startup, it's, there's a huge opportunity right now because a lot of the established vendors are lacking tremendously behind. You have a whole new generation of much more consumer-friendly, consumer-oriented CIOs and executives …”