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Future Proofing Your Sales Team

Samantha DeStefano, Vice President of Enterprise Sales at Upwork

Samantha DeStefano
Vice President of Enterprise Sales, Upwork



Ready to take your revenue to new heights?

Photograph of a sales team sitting at a table in a glass conference room
Photograph of a sales team sitting at a table in a glass conference room

One of the most remarkable trends to arise from the work from home shift has been the level of executive involvement in enterprise sales. Prior to COVID-19, executives sometimes engaged in the buying process. Today, they are heavily involved to ensure that budgets are focused on the right purchases.

As the Vice President of Enterprise Sales at Upwork, I have seen how this trend has evolved sales tactics. Economic uncertainty has impacted both the budgets and business goals of customers, causing effective sellers to become multi-threaded in product positioning. I explain this further in my recent interview on The Forecast.

The best sales messages in this new landscape must convey how the product will help the customer achieve their immediate needs much more quickly. On top of that, sellers must convince numerous stakeholders at each company as to the value of the product. 

Social selling has arrived 

Most customers today learn as much as they can about a product before they engage with a sales rep. This means that sales leaders should understand their brand messaging and align  with marketing to ensure a smooth, cohesive customer journey. 

More importantly, they should leverage current customers. Those customers are your greatest asset in sales because they can network and connect you to other relevant personas. Leverage that. For example, if you have a chief marketing officer as a client,  they probably know other CMOs at similarly sized companies. A few introductions could boost your pipeline. Prospective customers also will look to your current customers to decide whether your product is valuable to them. Being proactive about evoking this conversation is a game changer.

The buyer journey is changing

As executives focus on budget efficiency this year, sellers need to approach customers with surgical precision. 

Sales should  identify key stakeholders with every prospect, including executives, and tailor sales messages to the individuals. Consider how you will identify the needs of each buyer, and communicate the value that you add to every person at the account.

When coaching sales reps, it's important to collaborate on answering these questions:

  • Out of all your accounts, what are the top priorities?
  • What are the specific initiatives of my prospects?
  • Who are the target contacts we’re going after?
  • How can we impact this business and show value immediately?
  • How can we best communicate that value to them?

Decide how you and your team will measure each of your next steps. At Upwork, we’ve tightened  this process by asking our reps what their next move is, why it’s their next move, and how they’ll execute that step. 

Sharper skills for the virtual world

Having tools is extremely important as a leader and given recent events, those tools need a makeover. Here are three valuable skills you should adopt this year:

  • Visibility. We need visibility into our forecast and into the whitespace within current accounts to be able to measure progress towards our goals. And we can’t just walk the halls and overhead conversations from our teams. I suggest recording your calls and reviewing them with your team to unpack what worked and what didn’t in a sales cycle. This information drives efficiency in future sales. 
  • Relationships. People crave human connection right now. Find ways to create deeper and more meaningful relationships. For example, asking your customers for advice can accomplish this. People are more willing to help now, and gaining those insights helps you to understand what your buyers want. 
  • Trust. In this virtual environment, we can’t see one another or understand what each team member is doing day to day. For many, our tasks have increased, but our hours have not. Only with built-in trust can teams flourish—micromanaging from a distance is stressful and counter productive.

The future of enterprise sales

Though it sometimes hasn’t seemed so in the past year, the future of enterprise sales is bright. Don’t get distracted. Stay focused, strengthen your multithreading skills, and enjoy a more efficient and rewarding 2021. 

Interested in more episodes of The Forecast?

Watch these episodes featuring top sales executives and learn how your peers are navigating the virtual sales landscape: