The Twenty Minute VC

Mire CRO Zhenya Loginov: Hiring Tips for Sales; Why Dropbox Lost Enterprise | 20VC #900

Zhenya Loginov is the CRO @ Miro, the leading visual collaboration platform that helps bring teams together and meaningfully improves the way people work. At Miro, he runs the go-to-market team of 700+ people across 11 global offices. Prior to Miro, Zhenya was the COO @ Segment where he built and ran the global go-to-market team of 200+ people, expanded the product-market fit into the Enterprise and grew revenue 6x, leading to their acquisition by Twilio for $3.2Bn. Finally, before Segment, Zhenya led a 100-person team at Dropbox across numerous different functional areas. -------------------------------------------------- Timestamps: 0:00 Zhenya's background 1:23 Biggest learnings from Segment and Dropbox 2:20 When to move to enterprise 3:27 Can you do PLG and enterprise at the same time? 5:40 Why didn't Dropbox win enterprise? 6:50 Biggest takeaway from Segment 9:00 What is a Sales Playbook? 12:30 When to hire a Head of Sales 14:17 Most common things that go wrong with PLG 17:22 Biggest resource conflicts at Miro today 20:20 What traits to look for in a Sales Leader 23:16 Hiring for roles in fields in which you're not an expert 24:56 How do you structure hiring process? 33:00 Enterprise Sales Leaders vs. PLG Sales Leaders 34:07 Do you use case studies when hiring? 35:12 Biggest hiring mistake Zhenya ever made 37:50 How to onboard the first Head of Sales 41:00 Biggest signs you hired the wrong person as Head of Sales 43:22 How to communicate concerns new hire that's underperforming 44:42 How to structure deal reviews 47:48 The ideal relationship between CRO and Head of Sales 50:03 How to implement structure without losing agility 53:58 Quick Fire Round -------------------------------------------------- In Today’s Episode with Zhenya Loginov You Will Learn: 1.) Entry into Sales as an Outsider: How Zhenya made his way into sales as an outsider and came to be one of the most powerful revenue leaders today with Miro? What are 1-2 of the biggest takeaways for Zhenya from his time at Segment and Dropbox? How did they impact his mindset today? Why did Dropbox not win the enterprise when they had the chance? What mistakes did they make? 2.) The Sales Playbook: What, Why and How: What does “the sales playbook" mean to Zhenya? Does the founder need to be the one to create the sales playbook? What are the signs that the founders needs to bring in their first sales hire? Should this sales hire be a sales leader or more junior sales rep? Is is possible to run a PLG and enterprise sales motion at the same time in the early days of the company? What do many founders misunderstand when contemplating adopting an enterprise sales strategy? 3.) Hiring the Team: How does Zhenya structure the interview process for new sales hires? Zhenya spends 5 hours with each candidate, what does he look to get out of each meeting? How does Zhenya break down the criteria for what he wants to see? What are some examples of this? How does Zhenya test to determine if the candidate has these criteria? What questions does he find to be most revealing? Why does Zhenya find case studies to not be useful? How does Zhenya use interview panels to ensure he makes the right hiring decision? Who is on the panel? At what stage do they meet the candidate? How does Zhenya like to use the panel? 4.) Laying the Groundwork: The Onboarding Process: What is the right way to structure the onboarding process for all new sales hires? What are some early signs that a new sales hire is not working? What can sales leaders do to ensure new reps get “early wins” on the board? What can leadership do to ensure the sales team has good cross-functional communication across the org? What works? What does not work? What are some of the biggest challenges of running a remote sales team? -------------------------------------------------- #ZhenyaLoginov #HarryStebbings #20VC #salestips #businessadvice #founder #miro #dropbox #business #salestraining #salesmanagement #salesmotivation #productledgrowth #enterprisesales #saas #saassales

Harry StebbingshostZhenya Loginovguest

Jun 21, 20221h 0mWatch on YouTube ↗

WHAT IT’S REALLY ABOUT

Miro CRO on PLG, enterprise timing, and hiring transformative sales leaders

Miro CRO Zhenya Loginov reflects on lessons from Dropbox, Segment and Miro, focusing on how to balance PLG with enterprise sales and why Dropbox missed its enterprise moment. He argues that winning enterprise requires full‑company commitment, but sequencing matters: nail PLG first if you can, then layer on enterprise early enough to not miss the market. A large portion of the conversation dives into how to hire and onboard senior sales leaders, including why founders should bring in a head of sales early, how to structure rigorous hiring processes, and what red flags to watch in the first 90 days. He also covers deal reviews, international expansion, remote sales culture, and the ideal relationship between CROs, heads of sales, and product‑led growth teams.

IDEAS WORTH REMEMBERING

5 ideas

Winning enterprise requires full‑company commitment, not just a sales team push.

Loginov explains Dropbox failed to dominate enterprise because the CEO, product, engineering, and culture never fully embraced enterprise and sales as core to the strategy, leading to missed timing and fragmented leadership.

Sequence PLG and enterprise carefully: nail PLG first if possible, but start enterprise early enough.

He believes the best model is PLG + enterprise, but warns that enterprise capabilities take years to build; start too early and you become a pure sales‑led company, start too late and you miss the market window, as he thinks happened at Asana and Dropbox.

Hire a head of sales early—once you have initial product‑market fit—not junior reps.

After the founder closes the first deals (up to roughly $1M ARR), Loginov recommends hiring a head of sales who can build the playbook and organization, arguing junior reps mainly consume founder bandwidth while strong leaders create it.

Design a rigorous, structured hiring process with clear must‑have criteria.

He sets 3–5 resume‑screen must‑haves (e.g., team size led, ARR stage, enterprise deal experience) and ruthlessly disqualifies candidates lacking any; he then spends 4–5 hours in structured, experience‑based interviews before sending them to a tailored panel.

Onboard leaders by freeing their first month and forcing broad relationship‑building.

For new heads of sales, he intentionally removes immediate delivery pressure so they can learn the product and meet future cross‑functional partners (e.g., engineering, product) first, plus assigns one low‑hanging project to quickly prove value.

WORDS WORTH SAVING

5 quotes

At Dropbox we had an opportunity to be Dropbox for the enterprise, and we sort of lost this opportunity to other companies.

— Zhenya Loginov

In the long run, the best business model you can have is PLG plus enterprise.

— Zhenya Loginov

I usually look for somebody who knows 70% of the job but is really passionate about getting the other 30%.

— Zhenya Loginov

If you don’t see any results delivered in the first three months, that’s a big red flag for me.

— Zhenya Loginov

Your job as a leader is to figure out how to either have the buy‑in or change the process so that the buy‑in is there.

— Zhenya Loginov

Lessons from Dropbox and Segment on enterprise and sales leadershipBalancing PLG and enterprise: sequencing, structure, and avoiding internal conflictFounders’ role vs. head of sales in creating the sales playbookHiring philosophy and process design for senior sales and revenue leadersOnboarding new sales leaders and identifying early signs of mis‑hireRunning effective deal reviews and fostering learning in sales teamsInternational expansion, remote sales culture, and the evolving CRO role

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