Tips for scaling Sales Teams with Matt Bress, VP of Sales Simplifeye

Building the Sales Machine’s Q & A series is focused on sales leaders out there in the real world building and scaling high tech sales teams.  We aim to bring you the most practical and operational tips from down in the trenches.

For today’s Q & A, we’re following up with the third part of our interview with Matt Bress, VP of Sales of Simplifeye, a mobile technology platform to help doctors run their practices.


 Best tip for sales teams that are scaling?

Sales leaders will often find themselves under top-down pressure to scale in order to hit organizational goals. It is the responsibility of a good sales leader to balance the desire to scale with the ability and readiness to scale, and to pushback if it is indeed a premature expectation. Few things are more disruptive and costly to a company than scaling a sales org that is not prepared – we’ve all heard the horror stories. So the first and best tip for scaling is knowing when to and when you’re not ready.

Do not scale because your existing team is under-achieving and you need more headcount to attain high-level goals. If the team is not hitting goals there is at least one fundamental problem that needs to be addressed first (bad hiring, poor coaching, inadequate resources, unrealistic goals, etc). Scaling on top of these problems only compound them and are a death sentence (imagine constructing a skyscraper on faulty foundation). Identify the root of the under-performance and remedy before you consider scaling.

Make sure your success is replicable. Perhaps you have hit goal over the last two quarters, but has that success been achieved in a predictable and repeatable manner? If your org hit goal on the back of one or two really big deals, that is a red-flag. If most of your reps are missing goal, but you have a handful of rock-stars that carry the team, that is a red-flag. If your successful reps lack consistency and all employ different approaches to obtain their success, that is a red-flag. Make sure you have a play that you are training and coaching your reps to execute and that this play leads to successful achievement.

Have a plan for management. One of the biggest mistakes that young sales orgs make when scaling is an underestimation of management personnel. The classic misstep is realizing you need another manager and promoting the best performing sales rep. PLEASE, do not conflate past sales success with future management success! In fact, most of the traits that lead a rep to be the highest performing rep do not overlap with the traits needed to be a high performing manager. Most high-performing sales reps thrive on their ability to control their own success – as a manager, their success will be dependent on others, and that can be difficult for many reps. In addition, most high-performing sales reps have not truly struggled in the way that the majority of other reps inevitably will – lacking this experience actually makes it very challenging to identify with and support struggling team members. The discrepancies go on and on…. The point is not to necessarily disqualify your top reps, but rather, step back and really understand what makes a great manager and then triage your current team for who best exemplifies these competencies. I’m a big proponent of making internal promotions early on rather than hiring external managers, but if you are not confident you have management talent on your team, it’s better than elevating a good rep to a role where they are not set up for success.

Finally, before you scale you must not only demonstrate repeatability in your sales process, but confidence in your ability to repeat your training process. With a growing team, you will likely not be able to personally train new hires – consider grooming someone to be a training manager who is able to do this effectively in your place month in and month out. Make sure you have a new-hire onboarding checklist, training materials & curriculum, education about company & sales values, and  guidelines for graduation from training. An unprepared or mismanaged training process for new-hires will irredeemably taint all the incredible talent you’ve recruited and are depending on to drive the productivity you hope to achieve.


1bbcf47Matt Bress started his sales career at Single Platform as an AE, and rose through the ranks to sales manager, sales training manager, senior sales manager, and eventually Head of Sales.  Since they he went on to lead as the VP of Sales at Lofty, which was recently acquired.  He now leads the sales team for Simplifeye, a mobile technology company making it easier for doctors to run their practices and communicate with patients.

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