How to Manage Your First VP of Sales

This post originally appeared on Saastr.com.

Managing a sales leader for the first time can be quite a challenge for any CEO – This article is intended as a basic guide for ensuring that your sales dragon doesn’t use their powers of persuasion to obfuscate your reality.

Whether your head of sales is a seasoned veteran or a first-time manager, you should expect more than, “Weaving the blanket of revenue that keeps you warm at night.”, in response to a question about what sales is doing.

As CEO you must set the agenda for executive inspection and the following will give you a big head-start.

For the sake of brevity I have listed a cadence of inspection points in the table below and pointed out the things to be wary of at the bottom of each.

As an overarching theme I would encourage you to augment this list with business specific metrics and implement a standard, period-over-period reporting cadence that will allow a clear understanding of sales performance. It is worth saying that it is never too early to have the following data, so if you can’t get your hands on it, you should look at enabling resources (A sales operations headcount + reporting tools) and make it happen ASAP.

Weekly 1:1s with every rep

Pipeline coverage and quality
Attainment and plan to close gap
Downgrades, Slips, Neglected deals
Obstacles to success
Focus deals
Forecast Commit/Best Case (done either group or 1:1)

Why and what you should inspect: You should be asking what has changed week on week and why. Your sales leader should be able to name the items that have changed and why. Importantly, she should be able to articulate an action plan.

Problem signs:

Your leader can’t name the deals that matter within this period {or can’t give you a direct update on them, he has to ask someone on his team – Jason/ed.}
Excuses are made for deal slippage
Execs outside the sales org are not being leveraged to close deals (Esp. enterprise)

Monthly Ops Review

‘Lead to close’ pipeline stage conversion metrics (find where the funnel is leaking)

‘Deals by lead source’ review (ensure demand gen $ are being well spent)

Pipeline velocity (are we getting more or less efficient?)

Attainment by rep (month on month comparative to learn ramp patterns and catch failing reps early)

Productivity per rep (MRR/Headcount to make sure you are meeting the board plan)

Loss reason reviews (react quickly to patterns)

SDR production (watch for attainment against # of opportunities but falling short on $ targets)

Forecast and forecast accuracy (look at 90/60/30 forecast accuracy snapshots)

Why and what you should inspect: The operations review is mission control for understanding the key dynamics in your business – Marketing spend efficacy; Sales efficiency; Predictability. You should be checking that marketing is feeding sales per the plan, that reps are being enabled and ramped to plan and that your sales leader’s forecast can be trusted. It is also an opportunity to get product/GTM feedback from losses.

Problem signs:

Your sales leader can’t pinpoint root cause of funnel issues
Your sales leader can’t explain sales velocity changes.
‘Forecast to actual’ accuracy varies widely
No sensible plan to close attainment gap (especially deflecting responsibility)

Quarterly review

Review all ops items above for quarter over quarter
Review progress against territory coverage plan
Hiring plan to actuals
Review development/enablement plans

Why and what you should inspect: The QBR is a checkpoint for ensuring that the plan is working and that you have the right resources in place to execute it.

Problem signs: