To build a winning sales team, and avoid making deadly mistakes, you need a scalable, predictable, and data-driven approach.


Mistake #1: Hiring salespeople with your gut

Hiring rock star sales people is the most important step in building a winning sales team. Yet, so many organizations “wing” the entire hiring process.

Every sales context is different and, thus, every company has a different ideal hiring profile. Appreciate the uniqueness of your sales context, establish a theory of the hiring criteria that will work for you, and be disciplined about scoring every candidate against that criteria.

As you bring on salespeople, this process enables you to learn from your mistakes, iterate, and hone in on the perfect hiring profile.

Mistake #2: Under-utilizing the sales compensation plan

The sales compensation plan is the most under-appreciated tool in the CEO’s toolkit. In thinking back to the major strategic re-directions we navigated when I built the sales team at HubSpot, many of them were instigated by aligning the sales compensation plan with the desired strategic change.

Whether looking to enter a new industry, gain market share with a particular product line, or expand into a new geography, the sales compensation plan will be the most effective driver of change.

Mistake #3: Mis-aligning sales and marketing

Traditionally, sales and marketing are two groups that have not gotten along. Marketing perceives sales as a bunch of over-paid spoiled brats. Sales feels marketing sits around doing arts and crafts all day. In an age with the majority of buying journey’s starting online, this dysfunctional relationship is the kiss of death for a company.

A properly aligned sales and marketing team is a pre-requisite to a healthy business. Quantify the deliverables that marketing and sales should commit to one another. At HubSpot, we call this agreement the Sales and Marketing Service Level Agreement.

For example, marketing will deliver 1,500 leads per quarter that are contacts from Fortune 5000 companies within the retail, manufacturing, or technology industries. Sales will call these leads within 2 hours and convert 20% of them into sales pipeline within 30 days.

Measure the SLA progress and share the report daily with the entire team. You are now empowered to manage your sales and marketing funnel every day!

Mistake #4: Not planning far enough in advance

It takes 60-days to hire a new sales person, 90-days to ramp them to full productivity, and a four-month sales cycle to close a deal. If anything, these time frames may be on the aggressive side.

Yet, even with these assumptions, it takes nine-months from the decision to hire a new salesperson to the time when they are fully productive. Most of the hiring you are doing now is driving next year’s results. Plan ahead.

Mistake #5: Making forecasting, rather than coaching, the sales manager’s primary focus

Many sales managers spend the majority of their time managing the sales forecast and pipeline. This is a lost opportunity. Managers should spend the majority of their time coaching and developing their sales people.

Effective sales coaching increases sales productivity. The best coaches diagnose the one or two skills that will make the biggest difference in a salesperson’s performance and customize a coaching plan to that skill. They use metrics-driven sales coaching to conduct the diagnosis.

Mistake #6: Motivating through fear rather than metrics

I always ask candidates why they want to move on from their current employer. Many of them complain about the fear-based, micro-management of their current environment. This type of militant management style does not motivate sales people, especially Gen-Zs.

Instead, automate a daily dashboard stack ranking the team on total dials, total connects, total discovery calls, total demos, total sales, etc. Send the dashboard out every day to the entire sales and marketing team and include the CEO.

As a result, salespeople will be able to understand where they are gravitating from the “success blue-print” and self-diagnosis the areas in the funnel where they need work.

At the end of the day, the salesperson, sales manager, and the company are on the same team. Enabling everyone with the daily metrics will provide the motivation and discipline you desire.

Mistake #7: Letting new salespeople shadow top performers

“Welcome to our company, Bob. Do you remember our top salesperson, Sue? For your training, you are going to shadow her for two months.”

The shadowing approach to sales training is neither scalable nor predictable. In my experience, top salespeople are at the top for different reasons. They all bring a unique “super-power” to the table and lean into it heavily.

A ride-along sales training strategy may dissuade sales people from leaning into their super-power. It may also encourage them to pick up bad habits from their peers.

Instead, create a sales training process. Certify salespeople by quantifying their aptitude with each stage of the sales training process. Provide enough detail in the sales process to guide the salesperson but don’t make it too constraining that the salesperson cannot apply their “super-power”.

Mistake #8: Buying technology for management rather than the front-line salespeople

The majority of sales technology purchased over the last few decades has been purchased for the sales leader to conduct pipeline reviews and manage forecasts. The end result? The front-line salespeople do not use the software. Data integrity suffers and the original utility of the purchase is never realized.

There has been an explosion in sales technology that actually benefits the salesperson. It helps the salesperson sell faster by removing admin tasks and streamlines sales processes.

Integrating and implementing sales technology that benefits salespeople is the best path toward capturing the data that sales leaders need to run the business.

Mistake #9: Not experimenting enough

Every sales context is unique. Establish a baseline funnel. Form some theories on how the funnel can be improved. Devise and execute experiments. Iterate and improve.

  • Who do you sell your product to?
  • How complicated is your product?
  • How expensive is it?
  • Is your product sold direct or through partners?
  • Do most sales originate from inbound leads or outbound calls?

Varying answers to these questions call for varying approaches to the sale.


One of the most important keys to building a winning sales team is hiring the right sales talent. We teach you exactly how to do this in our free Sales Manager’s Ultimate Interview Guide.

About the author

Mark Roberge

Mark Roberge

Mark Roberge is Chief Revenue Officer of HubSpot Sales Products. Prior to this role,…

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