Navigating the Shift from Mid-Market to Enterprise Sales

How do you take a company that’s been winning in the SMB and mid-market world and help it thrive in the enterprise space? On today’s episode, I chat with Adam Block, Chief Revenue Officer at Motive. Adam shares the exact strategies his team used to move upstream without losing their core customers. If you're thinking about scaling your sales motion to land enterprise-level clients, this one is a must-listen.

Meet Adam Block

Adam Block is the CRO of Motive, a company that offers an AI-powered operations platform for the physical economy. Their platform helps businesses in sectors like logistics, construction, and energy run safer and more efficient operations. Motive is used by massive organizations such as FedEx, Halliburton, and Centos and they didn’t get there by accident. Adam and his team made a strategic decision to go enterprise, but they made sure not to break what was already working.

Going Enterprise Without Breaking Your Foundation

Adam shares that Motive's journey upstream started with demand from the market. Their technology was attracting attention from larger organizations across a variety of industries. But rather than jump too fast, the team took a thoughtful approach focused on three major pillars:

Do No Harm

The team made a commitment to keep serving existing customers while building out the infrastructure for enterprise. This meant careful segmentation, performance tracking, and redefining metrics to ensure success across the board.

Rewire the Business for Enterprise

From the sales process to customer support, Adam's team rebuilt their entire operation to accommodate longer sales cycles and more complex buying processes. They also rebranded from KeepTruckin to Motive to reflect their broader market.

Hire the Right People

Talent was key. Motive built a team of top-tier sellers and developed a farm system for internal promotion. With a focus on RAD, Resilience, Accountability, and Discipline, they created a high-performing culture that thrives under pressure.

Lessons from the Field

Adam shared practical tactics for leaders looking to move upmarket:

• Don't chase enterprise at the cost of your base. Segment carefully and let each part of your business do what it does best.
• Rebranding isn't just about a name, it's about a new story. Make sure it matches your long-term vision.
• Build internal mobility. Create opportunities for junior talent to grow into enterprise roles, which lowers hiring risk and strengthens your culture.

“You have to be bold. But you also have to be intentional.” – Adam Block

Resources

To learn more about Motive, visit GoMotive.com

Connect with Adam Block on LinkedIn Thinking about starting your own podcast? Check out Blue Mango Studios. Want help improving your sales skills? Join our Sales Mastermind Class.

Sponsorship Offers

1. This episode is brought to you in part by Hubspot.

With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.

2.  This episode is brought to you in part by LinkedIn.

Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.

3.  This episode is brought to you in part by the TSE Sales Foundation.

Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.

Credits

As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and Produced by Brightseed and Hill.