Building a Resilient Sales Organization
Sales Prospecting 10.13.2022

Building a Resilient Sales Organization

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In today’s episode, Mat Singer discusses the importance of building a resilient sales organization to maintain success in tough economic times. He shares his experience in coaching the sales reps to walk into renewal conversations to achieve success can involve using tactics such as quarterly business reviews and health checks. Tune in!

About the Guest

Mat Singer is recently promoted to Senior Vice President/ GM. Prior to this, he was the Vice President of Sales and Marketing at Upland Software, a global SaaS company based in Austin, TX. His team is responsible for marketing and selling nine of Upland’s thirty enterprise software products. Mat works virtually from the small mountain town of Grand Lake, CO, and has team members in the US, Canada, and the UK. Mat is nearing two and a half years with Upland and is a key part of helping develop and execute its growth strategy. 

Connect with Mat Singer

Key Takeaways

  • The most difficult aspect of coaching sales reps to see the big picture and grow their business is being analytical and breaking down revenue sources.
  • Renewal is a critical time for customers to purchase additional solutions, and new sellers often struggle with growth happening naturally rather than expecting it.
  • Coaching the sales reps to identify the bigger picture and plan their day-to-day and week-to-week is important to be successful.
  • The key skills that are tested in the interview and sales presentation are how quickly the candidate thinks and reacts, how well they handle objections, and how well they know their product.


“The formula for our growth [is] doing a great job of meeting the customer’s requirements. When you sell, implement effectively, and then earn that right to sell them more of the same product. That’s critical. Do a good job right from the beginning.” – Mat Singer


Highlights from the Episode

Can you share some insights into your role at Upland Software?

Mat does sales and marketing in Upland, which is a company that grows organically and through acquisitions. The company is global and has reached several countries for sales and acquisitions, including Canada, the UK, Australia, and North America, among many others.

How can the sales organization ensure growth in uncertain times?

The formula is to get it right from the beginning – do a great job of meeting the customer’s requirements when selling effectively and earn the right to sell them more of the same product. After doing this, explore the “hunting opportunity” by expanding to new buying centers. Maximize the benefit of your existing account base.

What are some of the challenges you could face while implementing this formula for growth?

One of the biggest challenges is being analytical and breaking down the data to realize where the revenue is coming from. It starts from making the customers happy to curating a strong Customer Success Program to invite renewals. There is abundant opportunity to expand during renewal, and it allows for dialogue on how to further help the customers’ businesses grow. The key is to have plans for every type of revenue that you want to maximize.

As a sales leader, how do you coach your team to be successful?

It all relates to being proactive. In Upland, there are two mechanisms. The first is conducting a Health Check, which is a structured engagement for the assessment of the usage of the software, configuration, and if the capabilities are being maximized. From here, we make recommendations. The second is running quarterly business reviews. This is the opportunity to get tactical and proactively maintain your reputation. The key to coaching the team is discipline in setting priorities and reinforcing them. The capable sellers, who are the right people on the team, are those who fit the company culture.

Is there a book, blog, newsletter, website, or video that you would recommend to our listeners?


Stuart Born – Owner and CEO of Born Outdoor

Kevin Gillies – Director, Strategic Sales at Miro


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