PODCAST 62: Managing People and Incentivizing Sales Team w/ Kathleen Roberge

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This week on the Sales Hacker podcast, we speak with Kathleen Roberge, Chief Revenue Officer (CRO) at Rocketrip.

She’s great at managing people and incentivizing teams. She’s so good, she gets results! She’ll also share her secrets on how to be a rockstar CRO.

If you missed episode 61, check it out here: PODCAST 61. Change the Job Process to Find the Right Candidate w/ Kathleen Roberge

What You’ll Learn

  • How to implement rapid experimentation
  • How to persuade people
  • What makes a great team
  • How to excite your team (and incentive them along the way)

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Show Agenda and Timestamps

  1. Show Introduction [00:09]
  2. About Kathleen Roberge: An Introduction [03:00]
  3. Thinking Outside the Manager’s Box [08:39]
  4. Persuasion Starts By Establishing Buy-In Early On [11:49]
  5. Teams Over Idea [12:53]
  6. How to Attract and Retain the Best Young Talent [22:39]
  7. Sam’s Corner [41:05]

Show Introduction

Sam Jacobs: Hey folks, it’s Sam Jacobs, your friendly neighborhood Sales Hacker Podcast host. Welcome to the show. We’ve got Kathleen Roberge, she’s the chief revenue officer at Rocketrip.

She’s an incredible leader and she has a number of great insights, both about how to manage people and how to incentivize teams, but also how to be a great chief revenue officer. It’s a great interview.

We’d like to thank our sponsors. We’ve got two sponsors on the show for you today. Conga is the leading end-to-end digital document transformation suite. With Conga, you can simplify documents, automate contracts, and execute e-signatures so you can focus on accelerating sales cycles and closing business faster.

Our second sponsor is Outreach, the leading sales engagement platform that enables sales reps to humanize their communications at scale, from automating the soul-sucking manual work that eats up selling time to providing action-oriented tips on what communications are working best. Outreach has your back.

About Katheen Roberge: An Introduction

Sam Jacobs: Kathleen is the new chief revenue officer at Rocketrip, but she’s a career CRO and sales leader. She spent 20 years growing technology companies through her focus on delivering strong go-to-market strategies, building demand gen engines, opening new channels of revenue and developing customer success and account management programs. She contributes regularly to thought leadership, participating in 20 to 30 speaking engagements annually and publishing lots and lots of articles.

​​Kathleen, welcome to the show.

Kathleen Roberge: ​Thank you, Sam. It’s great to be here.

Sam Jacobs: ​So tell us what Rocketrip is.

Kathleen Roberge: ​It’s a great concept. Rocketrip is actually a rewards platform incenting travelers to spend less on travel. Essentially, what we do is we present each traveler with a price to beat. If they go below that price, they keep half the savings and the company keeps half the savings. So it’s a win-win for everyone.

Thinking Outside the Manager’s Box

Sam Jacobs:​ What are some of the pillars of your management philosophy, your leadership philosophy, and maybe even your sales philosophy?

Kathleen Roberge:​ One thing is what I call rapid experimentation. It’s taking risks and trying new things that the company’s never done before. I always say that the risk of not experimenting is greater than the risk of failure. And these don’t have to be big, disruptive risks or ideas. It’s more about making smaller improvements and testing the assumptions very quickly.

​​Another philosophy is, don’t be afraid to… try new things, think out of the box. I’ve done things like make people earn their spots on my sales team. ​​I’ve done some really crazy things with distributed work environments and not being so fixated on having everyone in the office.

Never limit yourself and always be thinking of what works best for the company, even if it’s not the traditional, conventional way to do things.

Persuasion Starts By Establishing Buy-In Early On

Sam Jacobs:​ Do you have a way of persuading people?

Kathleen Roberge:​ I’m a pretty transparent person and when I start with a company, I have a very frank conversation with the CEO, and sometimes even the board, to let them know that I am going to experiment and that’s what I was brought in to do. I try to get their buy-in, even before I come on board, that I’m going to be asking for their commitment and their buy-in on some non-traditional things.

​​If they have confidence in you and they are willing to let you take some experiments, that upfront and frankly, if they said, no, we’re not going to let you experiment, I would know that this wouldn’t be the environment that I would thrive in. So it’s good to have that conversation early and upfront.

Teams Over Idea

Sam Jacobs:​​ “Teams Over Idea.” Tell us what you mean by that concept.

Kathleen Roberge:​ ​Sometimes people think, especially with startups, that it’s all about the idea and how great the idea is. But one concept that I always found is, you can have the best idea ever, but if you have a team that can’t execute, what good does it do you?

It’s always better to have a great team than a great idea. They’ll figure out a way to execute and a way to come up with an even better idea if they need it. It’s really more about the people that you hire, than the actual idea itself.

Sam Jacobs:​ ​What do you think the mechanisms are for building a great team? What are the strategies that you use to make a team great in the first place?

Kathleen Roberge: ​The whole idea about finding ways to motivate your team–for everyone, it’s different. Invest time in your team and figure out what is the one thing that gets them really excited? Is it money? Is it recognition? And once you determine that, you start to play with those levers and really incentivize people based on what they’re motivated to do.

RELATED: How To Manage A Sales Team: 12 Expert Tips For Success

How to Attract and Retain the Best Young Talent

Sam Jacobs:​ ​Part of your management philosophy and leadership style is developing young talent. Working with, I guess we can call them Millennials, but really, the dominant laborers in the workforce now, but talk to us about your perspective, relative to conventional wisdom and how you think about engaging and motivating these folks.

Kathleen Roberge: I’m a fan of Millennials and I’m not afraid to say it. I have many, many colleagues and peers that find the behavior of Millennials frustrating. Typically, they’re labeled as needy, entitled, they’re not loyal, they’re casual workers. And I frankly, have seen the complete opposite.

​​I don’t look at them as needy, I just think they need a lot of feedback and they want to build trust with their employer and that’s good.

They’re pushing the bar to cause companies to have more friendly, engaging, flexible environments, which is what we need in order to attract and retain the best talent.

Sam Jacobs:​ As you’re thinking about attracting and retaining, is it just about incentives for you? What’s the kind of work culture that you’re building to make sure that you do engage the rising stars of the workforce and make it a productive place?

Kathleen Roberge: ​It’s not about just incentives. Not at all, actually. There’s a large part of it that is about the culture and the level of engagement that you have with these employees, asking for their input, letting them be a voice in the organization. Especially if you see an employee who has a creative idea, let them speak it. Don’t speak it on their behalf, invite them to an executive meeting, have them share an idea, give them some exposure. And the best thing that you can do is give them some recognition.

I’m a big fan of the environment around them–create one that allows them to thrive. That’s not just motivating them with incentives; that’s recognizing them and giving them that voice in the company, so they feel like they’re a contributor.

Sam’s Corner

Sam Jacobs: Hi, team, it’s Sam Jacobs. This is Sam’s corner. Another fantastic interview, Kathleen Roberge, what a track record. She joins companies and something good happens.

What We Learned

  • How to implement rapid experimentation
  • How to persuade people
  • What makes a great team
  • How to excite your team (and incentive them along the way)

Don’t miss episode 63

This has been a great show. Before we go, we want to thank our sponsors. Conga is the leading end-to-end digital document transformation suite. With Conga you can simplify documents, automate contracts, and execute esignatures. Our second sponsor is Outreach. Outreach is the leading sales engagement platform.

If you want to reach out to me with feedback, you can reach me on LinkedIn.

This has been the Sales Hacker Podcast. And that’s all I’ve got for now. We’ll talk to you next time.

This is a sponsored guest post from a Sales Hacker partner.

Sam Jacobs is the Founder of Aqueduct Revenue Advisors and the New York Revenue Collective and regarded as one of the top start-up CROs in the tech community.

He has has over 15 years of experience scaling companies from post-revenue to ~$300M, has helped raise over $400M in institutional capital, and has helped companies of all sizes achieve an average annualized revenue growth rate of 48% over the last 15 years.