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This or That: Real-Time Problem Solving for Navigating the Hardest Selling Environments

Sep 15, 2023
3 min read

In today's rapidly changing Sales landscape, sellers face numerous challenges that have made it one of the hardest environments to close deals in recent memory. In a recent episode of Sales Hacks with Xactly, This or That: Real-Time Problem Solving, a group of Xactly’s sales leaders Ryan Maggio, Taylor Wilding, and Brandyn Le-Lewis took part in the popular Index Card Challenge, sharing their insights on the current state of Sales and providing strategies for success in this challenging market. Here’s a recap of what was discussed.

A Challenging Sales Environment

Question: Why is this one of the hardest selling environments?

Brandyn answered by saying that one of the biggest difficulties lies in adapting to the new reality of the industry due to downstream effects of the COVID-19 pandemic. Taylor called out that workforces are smaller, and individuals are expected to do more with less. Additionally, decision-making processes have become more complex, with multiple stakeholders involved in making key decisions which draws out sales cycles.

Unlocking Potential in C Players

Question: If you have a C player with potential, what are some tactics to get them to an A player?

Taylor emphasized the importance of coaching, which should address specific aspects of performance such as prospecting, deal progression, and closing. Additionally, by setting them up for success in meetings with key stakeholders, sales leaders can help C players reach their full potential and contribute significantly to the team's success. For Brandyn, it’s all about finding out what’s motivating them, and structuring training around that. Also, by leveraging data and focusing on areas of opportunity and improvement, C-level players can progress quickly to A-level performers.

Leveraging Data and Personal Credibility

Question: How are you managing your sales forecast to maintain personal credibility as a sales leader?

Taylor dropped the “A” word, accountability, and how effectively managing the sales forecast plays a critical role in building accountability and maintaining personal credibility. Xactly Forecasting allows him to gain insights from the data, take strategic actions, and improve win rates.

Overcoming Stalled Deals

Question: When a deal is stalling, what are three things you do to jumpstart it?

Ryan said it's essential to focus on the following three strategies to overcome deal stalls:

  1. Build relationships. Fostering relationships with stakeholders is fundamental to progressing a deal. After all, people buy from people.
  2. Create champions within the organization. Those who can provide insight into the decision-making process and be an internal advocate to get the deal done.
  3. Engage in self-reflection. Sellers should reflect on their own actions and identify areas for improvement.

Driving Collaboration Between Sales and Rev Ops Teams

Question: How do you work with Revenue Operations to optimize the performance of salespeople?

Brandyn said driving collaboration between Sales and Revenue Operations (RevOps) teams can optimize the performance of salespeople. Hearing from their perspective what data should be incorporated into the sales cycle can help get deals over the finish line.

Ryan called out that there's a reason it's not called Sales Operations anymore. It's called Revenue Operations because you're looking at revenue as a whole, and not just the actual transactional sale. Rev Ops teams offer a macro-level perspective, providing guidance and feedback to reps, who are focused more on a micro-level and working in their individual swim lanes. This collaboration leads to better forecasting and deal management.

A Focus on Data Protection and Privacy

Question: Given a tough Sales environment, how is your approach to deals changing? What are you doing in this challenging market to make it easier for your customers?

Taylor said getting access earlier to the economic buyers seems to be the least path of resistance to getting deals across the line. Ryan called out how data protection and privacy have become crucial concerns for businesses, and how organizations no longer want to take risks. To address these concerns, the team agreed that sellers should arm economic buyers with a strong business case and salient points that can withstand scrutiny from CFOs. Educating reps on potential objections and ensuring a compelling value proposition early on are effective strategies for overcoming resistance.

Motivating Struggling Top Performers

Question: How do you motivate an individual rep that used to be a top performer but is struggling this quarter?

Taylor talked about how identifying areas for improvement and reinventing oneself helps. Leveraging video analysis to review sales calls can help identify specific areas for improvement. Going back to the fundamentals of selling and making adjustments based on changed circumstances can also reignite motivation and drive success.

The Sales Journey of Continuous Improvement

Throughout the episode, the speakers highlighted the importance of personal growth and development in Sales. They emphasized the need for mental fortitude, curiosity, and an introspective mindset to overcome obstacles and find unique solutions for each buyer. Learning from losses, correcting crutch words, and maintaining an internal Northstar all aid in achieving long-term sales success.In the end, by embracing change, focusing on continuous improvement, and leveraging data-driven insights, sales professionals can navigate the hardest selling environments and continue to achieve success.

Check out the full Sales Hacks episode of This or That: Real-Time Problem Solving.

And the debate still stands between the guys on whether a hot dog is a sandwich!

  • Forecasting
  • Sales Coaching and Motivation
  • Sales Performance Management
  • Sales Planning
Jordan Scott Headshot
Jordan Scott
Senior Manager, PR and Customer Communications

Jordan Scott is the Senior Manager of PR and Customer Communications at Xactly. She attended The University of California at Santa Cruz, and received degrees in Literature and Education.