September 8, 2021

Ready to join an early-stage startup as their first sales lead?

Jon Volk
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Ready to join an early-stage startup as their first sales lead?Ready to join an early-stage startup as their first sales lead?
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Editor's note: 

A startup’s first sales leader is one of the most consequential hires that founders can make. And it’s one of the most exciting roles a sales professional can take on. Not only is that person responsible for delivering the revenue that will propel the company toward its next fundraise, they are building the startup’s revenue system and culture.

There are many elements that go into the successful hiring and onboarding of a sales leader. Here at Unusual Ventures we have seen this firsthand, both from the hiring perspective, and the sales leadership perspective. For a startup’s founders, it represents the milestone of handing off a vital piece of their startup’s success. For the newly hired sales leader, it represents an incredible opportunity and challenge to build a professional, effective function from the ground up.

As a quick gut-check on the nature of the sales leader role, here are some of the questions for which leaders need to have a great answer. (You can find a full analysis of these questions — and answers — here in the field Guide)

  • Why are you interested in this role, and why this company?
  • We’re looking at a lot of candidates for this role, why are you the best fit for it based on where the company is in its journey?
  • What deal sizes have you sold to, on average, and range?
  • Tell me about the teams you’ve directly managed, and how you built them?
  • What would a 30-60-90 day plan look like for this role?
  • How should sales and client success/management work together?
  • How should sales and marketing work together at an early stage like this?
  • Do you work with sales engineers and sales support? If so, what role do they need to play at this stage when capital is finite?

And, from the founder’s perspective, this is what should be considered after the interview:

  • How many questions did they ask you?
  • How did they differentiate themselves from other candidates?
  • How much research did they do on your company/space coming into the call?
  • Did they make any excuses, blame others, or bash co-workers during the interview?
  • Does the candidate’s career progression make sense? Could they speak to how it is appropriate for this stage and this exact role?

Picking the right role (and bringing the right skills) is an enormously important — but subtle — process that we will explain in detail. To help sales leaders and founders hiring those sales leaders, we are announcing an exclusive event on September 30, 2021 that lays out the actionable tips and considerations that go into sales leadership success at early-stage startups.

The agenda will be:

  • What to look for when considering a sales leadership role at an early startup
  • Practical tips on how to identify early startups that have the best odds of raising follow-on rounds
  • Our analysis on the most exciting sectors for sales leaders across the B2B landscape
  • Q&A


This unique event will feature an in-depth, practical conversation between both sides of the table for hiring successful startup leaders. We will dive deep on the experience of finding and thriving at an early-stage startup. Because, for a prospective sales leader, no two opportunities are alike.

One of the most important factors is the sales system and culture that a new hire inherits. We will show prospective leaders what to look for and the steps we take for our portfolio startups to set those leaders up for success. Finally, we will provide real-world examples of different sectors and specific job opportunities that prospective leaders should consider.

Sales leaders at this exclusive event will hear from my firsthand experience as Director of Talent (and prior experience in sales recruiting at AppDynamics and Google), and learn the repeatable playbook for early-stage sales success that Dakota McKenzie (Sales GTM Leader, formerly sales rep at Segment and Databricks) has put into practice for numerous portfolio startups.

Apply here to attend the event, and join our newsletter community here for additional resources for building companies and careers!

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