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  February 20th, 2021 | Written by

How to Build an Entrepreneurial Sales Team

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  • In a typical firm with 100-500 employees, an average of 7 people are involved in most buying decisions.
  • Teams need to think creatively about how to approach accounts or companies with complex networks.

The front lines that your sales team steps into have never been more challenging. Hustling for a business no longer means spending long hours and perfecting the process. Cutting through the noise and clutter requires adopting the posture, mindset, and hustle of an entrepreneur.

In a typical firm with 100-500 employees, an average of 7 people are involved in most buying decisions. (Source: Gartner Group)

Today’s sales process takes 22% longer than 5 years ago. (Biznology)

So what do you do to shake things up to enable your team to find the decision maker quicker and educate and inspire the influencers to close the deal?

Incentivize risk-taking with reward

Encouraging and incentivizing risk-taking is a great place to start. Taking a bit of a risk, and thinking outside of the box, is what makes many entrepreneurs successful. Elon Musk was on the verge of bankruptcy when trying to keep SpaceX and Tesla afloat. The risk paid off, and the rise and grind mentality he brought to his team each day resulted in one of the most valuable energy companies in the world.

But in order to free teams up to take risks, they have to have the support of their manager. And, adding compensation incentives demonstrate that this is a mandate, not a mantra. 

Michael Ahearne of Harvard Business Review suggests implementing a multi-tiered sales targeting and compensation program that encourages risk-taking at the junior and senior levels. 

This type of compensation works well to incentivize top performers and minimize the negative impact of laggard performers. It’s a great way to foster a high-performing entrepreneurial sales environment.

Create a scalable sales infrastructure

In addition to risk-taking, teams need to think creatively about how to approach accounts or companies with complex networks of influencers and decision-makers. Some ideas can be:

Leverage applications like Rapportive and Email Hunter to quickly gather contact information to optimize the email capture process

Use a CRM like Salesforce or HubSpotCRM that allows your team to visibly organize different decision-makers and team members for target accounts in one location.

First, let your team experiment with these tools. Then, once best practices have been identified, take the time to document the workflows and places where tools such as these are most effective. 

Once your team has the tools and best practices in place, they can be turned loose to go after more challenging accounts. 

Rethink messaging and outreach 

Building rapport and connecting with the C-suite often requires innovative approaches to messaging and sales outreach. Boilerplate templates filled with generic phrases and industry buzzwords simply will not elicit a positive response. 

Sales teams must be encouraged to infuse their messaging and outreach with their personality and creative approaches. Not every “great idea” is going to be great. But that’s okay. As long as your sales team can self-reflect and quickly make changes so that they can use a different tactic with the next prospect. 

We suggest finding personalization opportunities in every outreach to encourage a response. Sales professionals who use personalization when contacts decision-makers at target accounts receive a 600% increased response rate

These types of strategies enable your team to find ownership in their deals – they’re humanizing each target account and beginning to develop a personal connection to the deal.

Automate and standardize workflows and technology 

Sales performance often increases when teams collaborate and have strong relationships with one another. One of the best, and most efficient, ways to foster collaboration and a spirit of entrepreneurship is with next-generation tools. GetAccept has spent a lot of time in the document tracking and sales automation world and we know the value of optimizing the sales cycle to increase deal conversion rates.

Sales visibility through the contract process is huge, because your sales team needs to know how the prospect is engaging with the proposal, regardless of what they’re communicating back to your team. 

Your proposals are being read frequently, but not closing. 

Prospects are not spending enough time on the pages most relevant to closing the deal 

Prospects are opening your proposals on Tuesdays, but not on Mondays or Fridays.

Knowing this information helps you craft more engaging, more successful documents that convert.

A sales workflow must allow for seamless integration of data between applications. As a sales team leader, your job should be to automate and optimize as much of the manual data process so your team can focus on what they are good at – selling. Your reps shouldn’t be digging through multiple applications to find a phone number they need. Integration between your prospecting tools, CRM, and sales document tracking needs to be smooth.

Socialize internal sales training

All successful entrepreneurs leverage mentors to avoid mistakes and seize hidden opportunities. Part of building an entrepreneurial sales team that is actually successful is connecting your underperforming team members with overperforming members.

Much like playoff brackets are developed in sports, where the #1 team is paired up against the worst team, and the #2 team is paired with the second-to-worst team, so should you build a mentorship bracket.

Rank your sales reps from highest performing to lowest performing. Then set up mentoring schedules for your best reps to help train, motivate, and support their mentees. Weekly coffee meetings between the two reps can result in big wins for the team:

The best sales reps feel simultaneously empowered and valued by you and the rest of management.

The “learning” sales reps feel like they’re being invested into and management wants them to succeed.

You socialize the mentoring and training process, thereby scaling sales empowerment and efficiency across the whole team.

Every quarter, refresh the bracket and re-pair the team. This will allow new relationships to form and learning sales reps to receive coaching from other team members who can provide new perspective and ideas.

As a manager, you’ll want to set up a way for your team to adopt these behaviors and add their own special touch so that it’s authentic. Leading a sales team is a demanding yet rewarding job. Seeing the team thrive under leadership that values risk, empowers team members, and removes roadblocks is highly satisfying and leads to improved morale. 

Try a few of these ideas this quarter and watch your reps mature into a successful entrepreneurial sales team.


Samir Smajic is the CEO and Founder of Get Accept, the all-in-one sales platform where you design, send, track and market your proposal to get more deals digitally signed.