Sizing Your Sales Team for Long Term Success

WEBINAR SERIES

Date: Wednesday, April 29 2026 (12pm-1pm Est)

Are you missing opportunities because your sales team is undersized for the markets you are in?

Is the cost of your sales team higher than it needs to be with an oversized team?

Most firms make decisions on adding or reducing the size of their sales teams based purely on affordability. This doesn’t factor in market potential and in many cases the impact on profit. It can put your company at a competitive disadvantage and will cause you to miss opportunities.

In this webinar you will learn how to determine if you have the right size team and make decisions on where and when to increase or decrease the size of your team to optimize your return and market potential.

We will help you determine what roles are most important for you to fill. Why bring in an expensive outside salesperson when you can have a much greater impact investing in resources to make your existing team more efficient, provide more outbound leads or get more from existing clients. Defining roles is the first step in developing a plan to hire the right person for the job.

We will cover:

Six ways to determine if your sales force is the right size.
The six most common ways Companies make decisions on sales force sizing and why they can be less effective.
How to factor in customer segmentation into your salesforce sizing decisions.
Four different market-based sales force sizing approaches.
How to determine what roles are best to fill when adding people to your sales team, (Account Executive, Account Manager, Outbound Sales Development Representative, Inside Sales Development Representative, Sales Administrative Support).
When using distributors, resellers or independent agents make sense.
What to consider when using distributors, resellers, or independent agents.

Meet Your Trainer

Ken Cheo

President and Owner of Our Sales Coach.

Ken Cheo, is the President and Owner of Our Sales Coach. Ken works with business owners, sales managers and select salespeople with guaranteed results for top-line sales growth. He helps companies develop an ideal client prospecting system where they can gain a strong market position and produce meetings with decision makers at ideal clients. Ken helps his clients develop a scalable and repeatable sales process that ensures they are not wasting time with people who don’t buy or buy from someone else. He works with business owners and sales managers on how to coach their sales teams so the changed behaviors and sales processes become habit and sustainable. Prior to creating the Our Sales Coach brand, Ken enjoyed over 20 years of sales and sales management experience. Ken has participated in speaking engagements and seminars on a variety of sales and marketing related subjects.

Bruce Stephan

Bruce Stephan brings 20+ years of real-world revenue leadership to the training room. As a Sales Trainer with Our Sales Coach, he works with sales teams and executives to close the gap between strategy and execution – building the habits, processes, and disciplines that drive consistent, measurable results.

Bruce’s background is not academic. He has led growth, go-to-market strategy, and commercial transformation across Fortune 1000, private equity, and mid-market companies – with a track record of double-digit revenue growth and meaningful EBITDA improvement. He knows what works because he has done it, repeatedly, across manufacturing, trade-based, and industrial organizations where margins are real, and performance is non-negotiable.

His training style mirrors his operating philosophy: direct, practical, and outcome-focused. Bruce doesn’t teach theory – he builds capability. He helps sales professionals and leaders identify where performance is being gained or lost, sharpen their value proposition, and install the disciplined execution habits that separate top performers from the rest.

A defining strength is his ability to simplify complexity – and his marketing background is a big part of why. Years spent crafting positioning, messaging, and go-to-market strategy taught Bruce how to communicate value in a way that gets noticed and feels personally relevant to the buyer. He brings that same discipline into the sales training room: helping teams move beyond features and benefits to articulate why they win in language that actually lands with the people they’re selling to.

He quickly diagnoses what’s slowing a team down, cuts through ambiguity, and gives people a clear picture of how to turn strong positioning into real revenue. Teams leave his sessions with clarity, not just content.

He believes results come from discipline, not inspiration. Clear priorities, defined processes, accountability, and consistent follow-through. His work is grounded in three principles: customer insight creates clarity, operational discipline creates leverage, and execution delivers results.

Bruce holds an MBA from the University of St. Thomas and a Bachelor of Science in Marketing from the University of Minnesota. He has worked with enterprise organizations, mid-sized companies, and hundreds of leaders across industries.