You Have to Train Reps 3-100+ They Won’t Train Themselves. (Updated)

There’s a slide I see again and again from start-ups:  2 of the early sales reps are at 100% of quota, sometimes 150%-200%.  And 8 others? 10%-40%.

What’s happening here?  Are 2 of the first 10 reps really so much better than the rest?  Well yes, probably.  You’ll continue to see that over time to some extent.  The top reps will way outperform the average reps.  But not this much.  So why, so often, do only 2 of the first 8-10 sales reps perform?  And the others perform so poorly vs. the 2 that are doing well?

Almost always there is a strong correlation to No Training.

The first 2 scaled reps you hire that hit plan (some may churn before then) get special training.  They get CEO training.  They get CTO training.  They sit next to the founders, the team, to everything.  They learn by osmosis and from the visionaries.

After that, typically, the CEO just needs to get back to work.  So she or he still helps reps 3-10, just not as much.  The informal, ongoing training fades into a little help the first week.  And then a tough cycle sets in.  Without training, reps 3-10 scale more slowly, if at all.  They miss their first quarter.  And they lose their confidence.  And they see the CEO sort of playing favorites with the 2 early reps that are doing well.  And they see the CEO sort of judging them for not scaling quickly.  And they fail.

Usually, this is sort of solved when you find a strong first VP of Sales.  She’ll figure out how to train the team, one way or another.  But 90% of CEOs are terrible at it, and/or simply don’t think enough about it.  And so we see reps 3-10, or reps-from-#3-until-The-VP-of-Sales-is-Hired … fail.

So what can you do?

• First, recognize you just have to train your sales team.  Forever, in general.  But you, as CEO, have to do it yourself at least until you have a true VP of Sales.  You have to join their first few sales calls.  You have to have weekly discussions where they can get their questions answered.  You gotta do it.
• Set up a weekly pipeline and stories meeting.  Have everyone in sales share tough deals they are working on, tough questions, and celebrate wins.  And review key losses.  This is a hack to train folks.  Have everyone in the meeting share the top deals they are working on, what the make-up and challenges in the deals are.  And also share stories from closed deals.  This is usually eye-opening once you do it and join it.
• Use a tool like Gong or Chorus to listen to their calls.  Do this.  It took me a while to realize how powerful it is to listen to the calls of reps 3-300.  And for CEOs, especially reps 3-10, the ones that you are still managing.  The first 2 reps, you will know what they say to prospects.  You’ll be in the trenches with them.  But reps 3-10, you won’t be next to them, helping on every deal.  So listen.  Force yourself to spend a few hours a week listening to their calls recorded in Gong or Chorus or other services built into Salesloft and other systems.  Some of them will say terrible things.  Most of them will say many wrong things.  This isn’t proactive training, per se.  But it’s an A+ way to spot issues, jump in, and help.
• Read their emails.  One way or another, attached to Salesforce using Mixmax, Salesloft or otherwise, or however it gets done … audit their emails every week.  Listening to their calls is even better, but this is a close second.
• Make their core deck and their collateral for them.  Unless you have a VP of Marketing or someone else making a core, approved customer deck — you have to make it for them.  Reps 3-300 will do it wrong, use outdated materials, etc., etc.
• Add weekly webinars for prospects, invite all of them — and make your scaled team members do them.  If you do a 30-60 minute webinar for all prospects each week, and have your 2 reps that are scaled + you + your head of marketing (if you have one) do a standing demo on the webinar followed by Q&A after … that will ensure at least one interaction with all prospects that attend is well done.  Just do this.  Every week.  Even if just 1 great prospect shows up, that’s OK.   These webinars will also be great training for the new folks.  They can watch the trained folks present, and importantly, hear prospect questions on the webinar after.
• Simplify your sales process.  This isn’t magic, but it can help.  Simplify to a 1-page contract.  Make pricing simple.  Get rid of non-standard discounting and other dramas that will confuse new reps.  Let them focus on helping prospects, not gaming deal sizes.

Try these 7 tips.  They will make a difference.  Maybe even help some of reps 3-10 hit quota.

(note: an updated SaaStr Classic post)