Why is it so hard to hire great sales leaders?
Lately, I’ve been working on sales leadership roles for high-growth software companies. So listening to this recent podcast was very helpful,
Chad Peets chatting with Harry Stebbings on the The Twenty Minute VC provided invaluable insights into exactly why this is such a challenging role.
Chad is considered one the global leaders in hiring for software sales and has with 25 years experience, so he really knows his stuff.
10 ideas for hiring sales leaders
Here are 10 ideas any scaleup can use when hiring for sales leaders:
Bringing too many stakeholders into the process will create conflicting signals. Streamline the process to a binary ‘yes’ or ‘no’ within 2 meetings with the sales team. And there’s no need to bring in the technical team.
Hire fast, but keep to your strict criteria. Otherwise you’ll panic if the roles are still open for too long and make bad decisions.
The CRO needs to be at the front leading the interviews and deeply involved in understanding the profile, not just signing off at the end.
Evidence matters more than energy. Has this person actually done the specific job you’re hiring for? Can they show you?
References are essential. Speak to previous managers.
And character over charisma. A rep who genuinely loves the day-to-day grind - the calls, the rejection, the repetition - will outlast the flashy hire every time.
CROs don’t typically take on another CRO role with early stage companies If they have been successful. (its a common client request find someone who previously built ABC to do it again).
If you’re pre revenue, hire an experienced sales person to build the playbook, don’t have a technical founder step into the sales role.
What makes a good salesperson in software has remained similar over the years BUT it’s a lot harder to find In 2026 as culture and work/life balance are being prioritised by the talent pool - this doesn’t make the most effective sales hire!
5 days in the office is non-negotiable for maximum productivity. (This is something that’s requested a lot more in London hiring right now).
Why this episode is worth your time
If you’re in sales or hiring for a sales role right now, this episode is worth your time. There’s loads more insider insights into how to build high-performing teams at scale, how to both support and create hunger among your sales team, and how sales and product should be working together better.
What are you seeing when you try to hire great sales talent? Is it getting harder to hire for? Drop your thoughts below.
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