A series of essays about sales, startups, & general banter by Nick Persico

Building A Productive Inside Sales Team

Note: This was originally posted over at Medium under "Sales Hacks"

Sales and product teams play two entirely different games and have no common definitions for success — why try to control and optimize them with the same set of rules?

It’s no secret that startup founders aren’t usually salespeople. They often fall into the crushing trap of treating their sales team as they would treat developers (or themselves). An inside sales team should operate as an entirely different company, bound by a different set of rules and expectations. The exception to this rule is culture.

Since most startup founders have little experience with sales, they look for guidance in sales books and blog posts just like this. It’s common for books and posts to reference two very popular movies about sales that I’m sure you’ve seen or heard of: Boiler Room and Glengarry Glen Ross.

These movies portray sales as a toxic environment that’s aggressive and under extreme pressure. This attitude may have worked when these movies were made, but they don’t work today.

Treating an inside sales team like they are treated in movies like Boiler Room or Glengarry Glen Ross is not going to fly. Just about the only part of those movies that I would take as constructive advice is hustle. However, hustle should not be confused with being an arrogant jackass to your prospects. Your salespeople are not selling to the buyer’s those movies represent. Today’s buyers are more knowledgeable, they have more access to information, and have more choices.

Your team needs to know how to sell without applying direct force, and making the environment in which they sell should be the same way. Below are some tips on how to manage your sales team throughout the week to optimize for high productivity with a positive culture.

More Hours ≠ More Sales

Holding your inside sales team to the same “hours worked” expectations as your product team will burn them out quick. They need to be on their game from the hours of 9AM-5PM selling your product. That’s it. Anything else will burn them out, and make them less effective when it counts.

Salespeople shouldn’t be working 60+ hour weeks and staying in the office late. Our top sales reps spend the least time in the office because they make it happen between 9AM-5PM. Once the clock hits 9AM, they know that they only have 8 hours to squeeze as much opportunity from prospects as possible. If you take a look around, I’d be willing to bet that average to below-average revenue generating salespeople spend the most time in the office.

A Typical Sales Week

You can have a super productive sales team without constantly being on their back to perform. Use Monday to be stern in setting goals and share this week’s focus, and use Fridays to congratulate success. Limit any “all hands” meetings in the middle of the week as much as possible.

Any quick chats you need to have with the sales team should be communicated individually or in very small groups for no longer than 10 minutes at a time. Try to disrupt the entire team as little as possible.

Here’s the schedule of how a typical sales week goes for us at Krossover:

  • Monday: Morning standup for no longer than 15 minutes, share the goals for the week and general updates/announcements. Rest of the day is selling.
  • Tuesday: Selling, nothing scheduled.
  • Wednesday: Do something to break up the week See “Do Something on Wednesday” below.
  • Thursday: Selling, nothing scheduled.
  • Friday: All sales stop at 4PM. Celebrate the week’s success

Do Something on Wednesday

Use Wednesdays to break up the week. It’s hump day, so try picking one of the following “events” to give everyone a well-deserved change of pace:

  • “Work From Home Wednesday” — Where the entire sales team works from home on Wednesday. I looked at three weeks of sales activity data from our team (calls/opportunities/revenue) and saw no difference on Wednesday versus the other days of the week. I only recommend this for sales teams with less than five people.
  • “West Coast Wednesday” — My personal favorite. The entire sales team comes in two hours late in the morning and focuses on their opportunities on the West Coast. It usually just turns into a normal day, but some reps will stay an hour later to catch the mid-afternoon on the West Coast.
  • Everyone Leaves at 3PM — Pretty simple. Make everyone leave the office at 3PM on Wednesday afternoon. We all have errands to run!

Train Your Team To Sell Everything

When I look at posts for sales jobs, I often see companies label them with some sort of specialized role. Titles like “Outbound Sales Specialist”, “Inbound Sales Specialist”, or some other specialized aspect of the sales process makes me scratch my head.

You should always train salespeople to sell your product in every way that its sold. Your salespeople should have the opportunity to sell any of your products in any way that it’s commonly sold.

That means that everyone’s pipeline should be a mixed bag of inbound, outbound, edge cases, or larger opportunities. This keeps things exciting, makes them better at all-around sales, and presents a daily challenge.

No one likes to be good at just one thing, help them become a master in all aspects of your sales process. It’s only going to help your team adapt to change as your company scales and new “specialized roles” become necessary.

HYWKA (“Hell Yeah, We Kick Ass!”)

Every sales team should have a Friday afternoon HYWKA (“Hell Yeah, We Kick Ass!”) standup to conclude the week. Every single week has a bright spot that should be congratulated.

Stop selling at 4PM, grab some beers from the fridge, and huddle around to share what kick ass things went on this week. Between each announcement there should be a thunderous round of applause and cheering. It sends everyone into the weekend on a positive note regardless of what happened that week, and keeps perspective of why you’re all there.

Here is a sample outline of “HYWKA” each week:


  • Welcome new hires, someone’s first closed deal, birthdays, etc.
  • Announce this week’s “Sales MVP” (revenue collected, booked, or some other key metric)
  • Look for someone who had their best week ever, share interesting metrics about it.
  • Share who is having success at the top of the funnel (new opportunities/pipeline), it shouldn’t always be about closed deals.
  • Give an update on who is leading the way for the month/quarter.

Entire Team

  • “This week we closed X deals, and collected X revenue”, only if you hit your goals. If you didn’t hit goals, talk about the pipeline the team created that will lead you to crushing the goal next week.
  • Look for the metric where the team broke a weekly record, or did an outstanding job (number of demos, calls, new pipeline, avg. deal size).
  • Share new customer growth, in terms of week-over-week or month-over-month growth for give higher level context.
  • Look forward to next week, and end things with a positive outlook on the future.

Your sales team’s jobs are stressful enough, why add to it with a stressful work environment? Unlike the movies, be better to your sales team and treat them with the respect they deserve. You’ll be rewarded with positive growth and a highly productive team!

Profile of Nick Persico

Nick Persico

Director of Sales at Close.com. Previous: Co-Founder of Smart Host (acquired), VP of Ops at Krossover (acquired), and sales at Sysco. Travel nerd, Baltimore Orioles and Ravens fan, and GIF enthusiast.