2 min read

3 Tips from Boston’s Top Sales Leaders

Pictured above: Mike is a 25 year veteran of the information technology industry.


What did we learn? Written by Mike Stankus, SVP of sales at Acquia, following the Sales Roundtable at Underscore’s recent Core Summit.

How should pilots be structured? How much should sales rely on marketing for leads? Why do deals slip and how can deal slippage be prevented?

These topics were top of mind for the CEOs and sales leaders attending the Sales Roundtable at Underscore’s Core Summit on October 18.

The session was deftly facilitated by Lauren Chacon, Chief Sales Officer at Endurance International Group and Ray Grady, President of CloudCraze. Lauren and Ray kicked off the session with the question “What keeps you up at night?”. The consensus answers among attendees: pilots, marketing and forecasting.

The key themes and take-aways from the discussion are as follows:

PILOTS are a necessary evil for early stage companies. If required to execute a pilot, best practices include 1) document and get agreement on success criteria, timeline, and checkpoints 2) charge an amount that at least covers your costs and 3) structure the deal so if the pilot is successful, the customer automatically roles into a long-term agreement — avoiding the need to go through two sale cycles.

Good news is that once you have a critical mass of customer references / proof points, pilots should no longer be necessary.

Everyone struggles with defining MARKETING’s contribution to sales, specifically around lead generation. Many attendees shared their experience building outbound capability to complement inbound leads. At some point, the quantity of inbound leads will fail to sustain growth. Best practices included creating separate inbound and outbound teams — each with its own targets.

Lead aging was also discussed, specifically at what point a lead should no longer be considered inbound. Consensus was leads older than six months belong in the outbound pool.

Our last topic was FORECASTING — more specifically deal slippage. Sales leaders get fired when deal slippage becomes a chronic issue. Though it’s impossible to completely eliminate deal slippage, improvements can be made through training sales reps how to ask tough questions and employing tactics such as validating (with the customer) in writing the approval / procurement process.

Another tactic to utilize for forecasted deals that are stalled or the customer has gone dark is the “Dear John”.

In conclusion, it was a privilege to share ideas with such a talented and accomplished group. Thank You Underscore for creating such a great event — and community.