It’s January, and Michelle Benfer is having a moment. “How do we want to operate together, this year? What are our guiding principles, and what do we want to hold ourselves to?” She says.

“Examples of this should be celebrated often”

Benfer looks at how values permeate through everything the team is doing.

“Managers really are that connection point, and one manager can impact 7,8,9,10 people. Which certainly is a hit to the culture.”

Michelle Benfer has transformed the scaling of technology companies into a revenue science. She currently serves at Francisco Partners, a leading technology-focused private equity firm. Previously, as the Chief Sales Officer at Bill, she managed a revenue portfolio of $1.3 billion with 500 employees under her leadership. Prior to that, she served as Vice President of Sales at HubSpot, where she led a team of 800 salespeople.

Her expertise spans both high-volume and enterprise sales, with a particular focus on developing effective sales management strategies and building sustainable revenue engines.

“At scale, the tactics you thought you’d execute fall short,” She says

Understanding Sales Dynamics: High-Volume vs. High-Value Sales

HubSpot's shift to a freemium model to penetrate the small business market exemplifies how adapting sales strategies can increase market reach. In contrast, selling \$10,000 deals versus \$1,000 deals requires different approaches, heavily reliant on pattern recognition and tactical execution by frontline managers.

“What's great about high volume sales is pattern recognition. One front line manager may sell more enterprise skews. One may have a super high volume / low ACV, but they missed their number a bunch. You might have another that keeps churning out reps.”

She says it all comes down to coach-ability. For micro and small businesses, product-led growth (PLG) motion is essential to build a sustainable moat and drive down-market conversions at scale.

A Real Sunk Cost

Benfer says if front line managers are not ramping effectively, it represents a major talent-side challenge and a real sunk cost to the organization. Beyond just knowing the product, managers need comprehensive training and development.

Benfer points out frontline managers have an “acute” pulse on the customer and macro-economic influences.

“Do your front line managers know when to go for the enterprise skew, and when to go for the pro skew? Are they selling multiple products up front? Are they taking more of a land and expand strategy? What is the quality of conversations with customers?”

“… Managers bring this forward, often loudly,” she says, Benfer points to Sandler and Mike Weinberg on manager effectiveness.

She says front line managers bring these issues up, "often loudly."

Do they have soft skills? Do they have mastery?

Benfer recommends diversity and bias training.

“How accurate is a managers forecast, what’s that variance? Ideally within 2-3% accuracy? That’s really important.”

According to Benfer, managers need to understand the Ideal Customer Profile (ICP) to tailor sales approaches effectively. For companies with an ACV of \$5,000 or below, automation of sales processes becomes crucial to maintain profitability.

“What is the Balance of strength of a manager? They might be crushing their numbers, have a great territory, and the best reps— but really they have 2 reps carrying them who have been banner reps for years.”

Poor management often leads to high turnover and cultural issues, evident through negative reviews on platforms like Glassdoor. Conversely, effective managers foster strong team cultures, aligning day-to-day tactics with overarching company goals.

Building a Sustainable Sales Culture

Sales methodology training once a year isn't enough. Benfer suggests a framework she was introduced to that has proven to be effective for her teams.

It's called RPA—Results, Pipeline, Activity— it's a format for checking in with reps. She also calls for high-quality 1:1 meetings. Front line managers need to focus on both soft skills and mastery of sales techniques, incorporating tools like Gong for call analysis and feedback.

Internal Hires & Fresh Perspectives

Benfer says internal hires have faster ramp-up times, which allows institutional knowledge to grow while providing immediate impact. Managers should discuss accelerators, clawbacks, and retention incentives with their teams to align expectations.

“But if you’re taking a look at your team and almost everyone has grown up with the company you might want to think about bringing in a fresh perspective to look at how things can be executed differently. Getting someone who can see things from fresh eyes and are grateful to be at this new company.”

Benfer mentions the optimal manager-to-rep ratio is typically 7:1. However, this may need adjustment based on sales cycle complexity and product diversity. Overextending managers with too many direct reports can dilute coaching effectiveness.

Conclusion

Investing in frontline talent should be a top priority. It needs to become woven into the fabric of how you operate. Create a continuous learning culture and strive to quantify the cost—of getting it wrong.