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How HR Can Support a Thriving Sales Organization

, |By Caitlin Allen

HR invests a lot of passion and resources in supporting managers across hiring, retention, compensation, and more. That’s especially true for sales teams, the revenue backbone of modern business.

In this podcast, we talk to seasoned executive Jesse Osborne, the VP of Global Sales Development at Tipalti, about what he’s learned about managing successful cohorts in a hyper-growth environment.

He’ll also share how HR professionals can best support thriving sales organizations.

Join us as we explore:

  • How to diversify and strengthen your staff as the company experiences growth
  • Developing a comprehensive comp plan and how to measure its success
  • Preparing your HR team for an economic downturn


Don’t miss the full episode: How HR Can Support a Thriving Inside Sales Organization.


“A resume only tells part of the story.” — Jesse Osborne

Your evolving hiring profile

It’s crucial for sales leaders to partner closely with HR from the very earliest stages. You might be an SME in your field, but they have the specialized experience to identify the core competencies and behaviors of the candidates who’ll perfectly mesh with your current vision.

Jesse is an exceptionally vibrant and energetic VP who has been working in the Bay Area market for twenty years.

He feels it’s vitally important to stay connected with HR and ensure your hiring profile adapts to the company’s changing needs. However, he’s always on the hunt for creative people with boundless curiosity.

The end-of-interview Q&A session is where Jesse really leans in to find those who are critical thinkers and problem solvers. He wants to see the wheels turning.

Especially for managers building a team from scratch, he considers it a deal breaker for any candidate who doesn’t take advantage of the chance to get answers or truly learn about exactly what they’re getting into.

Identifying future leaders

Another critical element of crafting the perfect crew is finding your lieutenants.

The ones who effortlessly solve problems and inspire trust — the person everyone goes to when they want a sympathetic ear and a solution that works. That’s an invaluable quality for growing successful company culture.

“In the early stages,” Jesse notes, “thinking about your leadership team, what roles they can fill, and what holes they can plug is extremely helpful.”

After identifying two key players in his first days at Tipalti over three years ago, he says they’re still by his side, and “I couldn’t do a thing without them.”

“One of the questions I love to ask is, ‘if you had a free hour on your calendar, what would you do?’” — Jesse Osborne


Wear whatever hat is necessary

Anyone who’s worked at a startup knows you need to be exceptionally well-rounded and willing to pitch in and do whatever it takes. And impressive big company experience doesn’t always translate to success in this arena.

That highly adaptive mindset is also vital for creating your sales playbook.

Jesse’s team had every intention of setting their processes down in a Google doc, with a table of contents and everything.

Instead, they collaborated on an interactive “rise guide” that’s a living road map, scalable and editable, and ever-changing to meet the needs of the business.

Simplifying the structure

In his first week at Tipalti, he dove into deciphering the needlessly complicated formulae of staff compensation. Jesse wanted to attract the best talent and he was “very passionate about ensuring they had a simple comp plan that could be described in 2-3 sentences.”

An SDR who’s constantly doing difficult equations to figure out how much they’re actually getting paid won’t be performing at full potential.

He takes the time to walk through the math carefully and examine every aspect of the unit economics behind the quotas. What’s reasonable and realistic for a large organization in boom times doesn’t line up with what’s ideal for a scrappy, early-stage startup.

“This is going to make you work differently, work smarter, and work harder. And I think it makes you better.” — Jesse Osborne


Transparency goes a long way

An eternal optimist, Jesse believes that a recession and a reset is on the horizon. “I think we’re all going to get tested in a very good way,” he states, and it’s going to result in revolutionary new thinking on efficiency and the unsustainability of eternal growth — “that’s the only metric that folks care about.”

Leveraging the current experience to evaluate and streamline your business functions will improve critical thinking and help build a bulwark against future downturns.

This won’t be the last one you go through, so take advantage of the essential lessons you can learn to come out stronger on the other side.

Blessings in disguise

Whenever the situation seems especially dire, Jesse advises listeners to remember that “things are usually worse in your head than they are in reality.”

He admired the resilience and dedication of HR pros who persevered through the creation of COVID protocols and the shift to remote or hybrid work. They provide an invaluable calmness and humanization that every business needs.

Keep it simple, stay in touch, and build those bridges.


To hear this episode, and many more like it, you can subscribe to The High Growth Matters Podcast on our website, Apple Podcasts, Spotify, or just search for The High Growth Matters Podcast in your favorite podcast player.