How Upserve Used InsightSquared to Optimize Their Sales, Grow From $2B to $4B in Sales Under Management in 6 Months

Providence-based Upserve, formerly Swipely, is on fire. At the end of 2014, the Software-as-a-Service provider of payments, analytics, and marketing tools for restaurants and other local businesses doubled their sales under management in 6 months: from $2B to $4B. InsightSquared recently had the pleasure of speaking with Matt Oley, the Vice President of Sales.

Upserve’s Challenge

In 2013, Upserve was growing fast, and rapidly adding members to their sales organization. Oley needed to identify the biggest opportunities to expedite growth, so he started investigating tools to help his 70 person sales team grow faster and more efficiently. The sales leadership at Upserve needed to easily identify coaching opportunities for their account executives (AEs) with data, and understand how to compare AE’s alongside one another.

How Upserve Solved Sales Coaching

After evaluating several analytics options, Upserve chose InsightSquared based on the software’s immediate time-to-value and sales best practice pre-built reporting. Upserve implemented the solution across the sales team within a few weeks. Quickly sales leaders at Upserve were able to use InsightSquared live in sales coaching and forecasting sessions.

Wins for Upserve:

  • 100% company growth
  • Decrease in sales cycle
  • Better visibility into pipeline
  • Improved sales coaching
  • Countless hours saved looking up and analyzing data

Individualized Rep Coaching and Higher Win Rates

With InsightSquared it’s now possible for sales leadership to be more attentive to each AE, because of the reports drill-down capabilities.  Oley can get reports for everyone on his team with just a few clicks.  This individualized focus allows him to create tailored coaching plans for each AE like never before.

“We use the InsightSquared Sales Funnel report, drilling in by account executive, to identify specific skill areas that need improvement such as prospecting, presenting and closing,” said Oley.  “By focusing on the proper area with each sales account executive, we have seen a substantial lift in individual win-rates, and subsequently, team win-rates.”

Reducing Sales Cycle and Purging Bad Pipeline

Oley and the team use InsightSquared to clean their pipeline and eliminate wasted time working bad opportunities. Oley uses the Monthly Sales Forecast report and Sales Cycle report to push AEs to remove opportunities they aren’t going to win from their pipeline. These issues become clear with InsightSquared, and the AE can then remove opportunities that are falsely inflating their pipeline.

This has led to a shorter sales cycle and an increase in bookings. “Without InsightSquared, we wouldn’t have as much clarity into where we should be focusing our sales efforts,” said Oley. “These reports have been helpful in developing a more disciplined approach to keeping a clean pipeline.”

A Data-Driven Culture Creates Peace of Mind

Before the team started using InsightSquared, data integrity was a concern.  “Making decisions with dirty data can be worse than using your gut,” Oley explained.  Since adopting InsightSquared, Oley no longer fears his team is operating off of dirty data. Oley said that the greatest benefit InsightSquared has provided him with is peace of mind.  “I know exactly where my pipeline is at all times and where I can expect to end each period.”   InsightSquared’s Forecasting report projects where future periods should end, allowing Oley to focus his efforts on the proper funnel stage instead of spreading himself thin across multiple areas.  “This saves me time that I can then allocate to other strategic initiatives like hiring, training, coaching, etc.,” said Oley.

Oley’s final words: “If you are looking for a great product that will save time, remove guesswork and supercharge your data, allowing you to make smarter decisions, you should use InsightSquared.”