As an account executive at freelance marketplace Upwork, Megan Williamson knows that transitioning from SMB to enterprise sales requires ample preparation. That’s why she encourages managers to set expectations with sales representatives and motivate them to actively engage during deal storms and forecasting sessions.
“Managers should empower reps to challenge thought processes during these discussions, as this will ultimately lead to better client conversations,” Williamson said.
Yet outlining parameters and encouraging participation are just a couple of ways managers can set reps up for success. According to Kathleen Glassett, director of enterprise sales at food-delivery service provider Grubhub, leaders should offer reps stretch assignments and help them create structured plans so they can anticipate the challenges that come with top-level clients, including navigating legal contracts and meeting higher buyer expectations.
From a leadership perspective, Glassett said endowing reps with adequate knowledge isn’t the only thing managers should consider. It’s also important to look for characteristics that prove a rep is ready to handle complex situations with decorum and efficiency.
“Consistency is everything, along with discipline, maturity and time management,” Glassett said.
Built In Chicago checked in with Williamson and Glassett to learn about the major differences between SMB and enterprise sales and what managers can do to support reps’ transition.
What changes will reps encounter when transitioning from SMB to enterprise sales?
One of the biggest differences is the complexity of both the deal and organizational structure. In SMB sales, there is often a direct line of approvals and much simpler access to the C-suite. On the other hand, the enterprise sales process is more complicated and offers little to no exposure to executives, yet they are the ones who make the final decision. A rep will need to be prepared to handle multiple perspectives and leverage champions while also navigating relationships within the prospect organization. Obtaining a “yes” in enterprise sales is often easier than everything that follows, such as security, budget approvals and vendor onboarding.
How can managers prepare reps to handle enterprise sales responsibilities?
Just as businesses have peaks and valleys, most sales reps experience the same when transitioning to enterprise sales from SMB. The deal cycles are often longer and more complex, which is why it’s essential for managers to set expectations for reps. Regardless of a rep’s tenure, managers should use the onboarding process to align reps’ expectations with the company’s sales cycle, pipeline progression and common hurdles. When a rep begins working with enterprises, their deal storms and forecasting sessions will tend to resemble a SMB process.
The deal cycles are often longer and more complex, which is why it’s essential for managers to set expectations for reps.”
How do you know when a rep is ready to start selling to enterprises?
There are two key considerations: confidence and a consistent display of strategic deal execution. Reps often grow their confidence over time. A rep shows they are ready to work with enterprises when they perform confidently with executives, easily handle objections related to business concerns and identify growth opportunities that are beneficial to both parties. When a rep does this consistently, they’re ready for enterprise sales.
What changes will reps encounter when transitioning from SMB to enterprise sales?
The biggest difference between SMB and enterprise sales is deal complexity and length of sales cycles. Having an SMB background enables sales reps to lay a strong foundation of best practices, which they’ll carry throughout their sales careers.
Enterprise deals are generally multi-faceted, involve buy-in from multiple stakeholders and require reps to listen closely to customers’ challenges and create connections across multiple products and services. Enterprise sales reps will spend more time in the weeds working with internal teams, vetting technology and navigating legal contracts. With enterprise brands, buyer expectations are generally higher and clients will expect reps to be polished and professional. Enterprise sales reps should also plan to take part in more in-person meetings, given the length of the process and significance of building relationships.
How can managers prepare reps to handle enterprise sales responsibilities?
Provide your reps with stretch assignments, so they can practice selling to larger organizations. Help them develop a structure to create a plan, anticipate pain points and think through the discovery process, according to buyer personas. Additionally, shadowing opportunities can accelerate the learning curve. An SMB rep should have a strong foundation for prospecting and cold calling, so giving them a senior enterprise rep as a mentor will help them ramp up more quickly.
It’s important to convey that enterprise sales deals are seldom the same, and objections vary based on needs and pain points. There are no shortcuts to success, so you must hold reps to a high degree of accountability, professionalism and self-discipline.
Consistency is everything, along with discipline, maturity and time management.”
How do you know when a rep is ready to start selling to enterprises?
I look for high attention to detail with a natural ability to learn complex ideas, strategies or technology. I also look for reps with a strong input to output ratio, which means they can achieve equivalent results through less activity by working intelligently and strategically.
From a presentation and polish standpoint, I look for reps who can think on their feet and adapt in real time with minimal changes in communication and body language. Lastly, consistent, positive feedback from customers and other teams go a long way.
