We know how many different balls a data-driven Sales VP has to keep up in the air simultaneously, but until you’ve really walked a mile in their shoes, it’s hard to actually grasp just how much a Sales VP has on his or her plate.

Well, we wanted to find out. While I couldn’t serve as a Sales VP, I did the next best thing – shadow Zorian Rotenberg, our VP of Sales here at InsightSquared, for a whole day! I stayed attached to his hip and was a fly on the wall as he went through his various responsibilities.

Read on to see just what a day in the life of a data-driven Sales VP really looks like:

7:00 am –

Coffee with a candidate we’re recruiting at a local Starbucks. Recruiting is one of the most important things a Sales VP must do. Our sales team is growing, and that means meeting with candidates for that new closing rep position you have available. After years spent interviewing and recruiting sales reps, you probably have a good idea of what attributes you want your closing reps to have. Test the candidate on their coachability, intelligence and passion for the position, among other things.

7:30 am –

Arrive at the office and review yesterday’s sales activity results. Sales activities are one of the few levers that Sales VPs can control, so this is a good metric to look at. Which reps made the most calls yesterday? Who was most efficient in converting calls to meetings booked and demos scheduled? Pulling up the nightly status email automatically generated in InsightSquared is a great place to start the day.

8:00 am –

Time for the pipeline review meeting with sales directors and managers. The Sales VP has to keep a constant eye on the inflow and outflow of the sales pipeline. As opportunities leave the pipeline – through both Closed-Won and Closed-Lost – the pipeline must be replenished with an inflow of new opportunities. This means working with marketing, the outbound prospecting team and channel partners to generate enough opportunities for sales to hit its quota. This is also a good time for an opportunity-by-opportunity review of key accounts.

9:00 am –

The next few hours have been blocked off for calls with the sales team or listening in on calls and taking notes for “film reviews” – both customer and prospect calls. When the Sales VP calls a recently signed customer to check in, that can send a message that your company will always be there for the client. Also call a prospect that you are trying to close and talk to the sales rep working that account to see if there is any way you can help advance a stalled opportunity – perhaps you have a relationship with the CEO at this company that you can leverage to help grease the wheels of this opportunity.

11:30 am –

Lunchtime. An important part of a Sales VP’s responsibility is meeting other sales execs for referrals and also for exchanging ideas and best practices. Today, Zorian is heading out for a lunch meeting with Mark Roberge, the Chief Revenue Officer at HubSpot. Over lunch, Mark will share his experience in growing a sales team from 1 to 200 reps – an expansion phase InsightSquared is currently in – while Zorian will help Mark solve a sales forecasting issue he’s been struggling with. There’s always room for improvement and opportunities to learn when you’re a Sales VP.

1:00 pm –

Back at the office, the early afternoon is a nice quiet time to get some uninterrupted work done. Today, Zorian has planned to dive into the existing sales model in an Excel spreadsheet and analyze to see how planned (and unplanned) variance is affecting sales performance, pipeline contribution, lead flow and the team’s overall win rate. It’s not enough for a Sales VP to simply focus on selling – there are dozens of analyses in which his attention is required to keep the overall sales machine churning.

2:30 pm –

Here at InsightSquared, we believe strongly in the importance of having a strong sales coaching culture. Throughout the week, Zorian will host both teamwide coaching sessions, as well as individual 1-on-1 sessions. Today, Zorian has dedicated an hour of sales coaching to work with Mike, a newly promoted closing rep. They have co-signed a plan to record calls for film review and help Mike improve on his demo skills and ramp up quickly.

3:30 pm –

More sales coaching! This time, Zorian, along with the Director of Sales Joe Caprio, will jointly lead a meeting with some of the newer prospecting reps. They will go over value propositions and positioning statements together, with each of the new reps chiming in to critique what they think is a best practice, and what is a poor tactic that doesn’t advance the call any further. Having open dialogue during sales coaching sessions is the best way to create a culture of engagement and enthusiasm among your reps.

4:30 pm –

Sales Forecasting meeting with your sales managers and top closing reps. The point of this meeting is to answer one simple question: how are we progressing against our sales goals? Are we going to hit our quota this month or quarter? Have each closing rep present their own personal forecast, while considering forecast killers they should be wary of and how their own personal forecasts will tie into the team’s sales forecast. If it looks like you are going to fall short of your goals, now’s a good time to start thinking about levers you can pull and campaigns you can run to help you make up that shortfall.

5:30 pm –

Boston has a thriving sales and tech community, so there are usually great events to attend in the evenings. Tonight’s event is especially exciting – a book launch hosted by Aaron Ross, the author of Predictable Revenue: Turn your Business into a Sales Machine with the $100 Million Best Practices of Salesforce.com. Zorian listened to Aaron and other local sales executives discuss “3 Big Ideas on Tripling your Sales,” and gained some insights and best practices that he just might put into practice right away.

7:30 pm –

Time to head home for dinner and to spend some time with the wife and kids. After dinner, Zorian will spend some time working, replying to unanswered emails and dive into some sales reports on InsightSquared. He will unplug around 9pm. After all, it’s important to step back and gain some perspective, read a new book on sales, marketing or leadership before tackling a new day tomorrow and doing it all over again.


There you have it, a day in the life of a very busy data-driven Sales VP. Zorian has to juggle many meetings, spends most of his day living in InsightSquared’s sales reports and has to manage his direct reports. Of course, Zorian also relishes this challenge, and wouldn’t have it any other way.

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