PODCAST 05: Moving Your Product (And Your Sales Team) Upmarket

On this episode of the Sales Hacker podcast, we talk with Rick Smolen, VP of Sales at Greenhouse Software about moving your product upmarket and how to sell your software to a big company.

What You’ll Learn

  • How to help a hyper-growth company move upmarket from mid-market into enterprise
  • What sales strategies and philosophies are necessary for enterprise sales
  • How a company must be designed to tackle the enterprise opportunity
  • Common errors of companies moving upmarket
  • The profile of a great enterprise seller and how that differs from different markets

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Show Agenda and Timestamps

1) Show introduction [00:10]

2) About Rick Smolen and Greenhouse[1:25]

3) Making a switch from Intralinks [3:26]

4) Growth in an SMB, mid-market, and enterprise [5:10]

5) Sales process, hiring, and territory management in enterprise sales [9:27]

6) The profile of a great Account Executive [13:25]

7) KPIs to track the success of an enterprise deal [20:00]

8) Pricing as an objection [25:30]

9) An impactful moment in Rick’s sales career [36:15]

10) Sam’s corner [39:00]

Sales Hacker Podcast—Sponsored by Node

Sam Jacobs: Hi, everyone, and welcome to the Sales Hacker podcast. I’m your host, Sam Jacobs, founder of the New York Revenue Collective.

Before we start, a quick thank you to this month’s Sales Hacker podcast sponsor Node. Node’s AI discovery platform can understand the meaning, context, and connection between any person or company by proactively surfacing opportunities that are highly relevant and personalized in real time.

Node is creating an entirely new paradigm for sales and marketing professions to grow pipeline and accelerate revenue philosophy.

Now on with the show.

Sam Jacobs: Hey everyone, it’s Sam Jacobs with the Sales Hacker podcast. Today we’ve got a good friend of mine, Rick Smolen. Rick is currently the VP of Sales at Greenhouse.

Prior to this, he spent 12.5 years at Intralinks where he began his sales career. He started as an individual contributor, spent three years as a frontline manager and then two years building out the go to market strategy in Hong Kong. The last four years there—managing the revenue generating business lines across North America. It’s been under a year since he joined Greenhouse. Welcome!

Rick Smolen: Thank you for having me, Sam!

About Rick Smolen and Greenhouse: Baseball Card Stats

Sam Jacobs: Very quickly, let’s go over your baseball card stats. Your name is Rick Smolen. Your title?

Rick Smolen: I’m the VP of Sales at Greenhouse Software.

Sam Jacobs: How big is Greenhouse?

Rick Smolen: We’re now over $30M ARR.

Sam Jacobs: Tell us what Greenhouse does.

Rick Smolen: Greenhouse is a SaaS company focused on Talent Acquisition.

We are relevant to companies that have challenges in four areas:

  1. Identifying quality talent for their organization.
  2. The actual process of making a hiring decision.
  3. Candidate experience.
  4. The ability to measure this process.

Sam Jacobs: How big is your organization?

Rick Smolen: We have 60 professionals on the sales team—SDR, Account Executives, and Sales Operations.

Making the Move From Intralinks to Greenhouse

Sam Jacobs: Intralinks is a big company—their revenue between $150M to $200M and you started off an as individual contributor. I’m just curious to know the factors that led to your decision of moving from a big company to a small company.

Rick Smolen: When I joined Intralinks it was a small company. I just wanted to learn and make a big impact. As a looked back at the journey as the company went from being a small one to a big one, I learnt so much out of it.

I wanted to repeat that kind of learning and start from a more elevated position where I can have an even bigger impact. I was very intent in joining a company like Greenhouse.

Sam Jacobs: How did you find Greenhouse?

Rick Smolen: I was speaking to recruiters and somebody that software to me in the past reached out to me—an AE that I’d built a relationship with. He tried getting me to join his company.

During the interview process, he left the company and asked me not to join the company! But he introduced me to the Head of Sales Operations at Greenhouse. This amazing company with a role for a VP of Sales, based out of New York. As I learnt more about the role, I was excited about what I saw and was fortunate enough to be selected for the position.

Sam Jacobs: I think it’s a very strong recommendation when someone’s recruiting you to be their boss! Congratulations on that.

How to Sell Your Software to a Big Company: SMB Vs. Enterprise

Sam Jacobs: Give us an idea of the dynamics of SMB vs. mid-market vs. enterprise. What are your growth prospects like?

Rick Smolen: When I joined the company, it was well orchestrated to do SMB and mid-market. All the sales process and tech was all set to do high-velocity selling. The focus was on the SDR-AE handoff, getting the discovery done, demo complete, and closing the deal and onto the next one.

There was a lot of ambition at the company to go upmarket and into enterprise sales. But the enterprise sales process was entirely different. There was some struggle to not lose the momentum with what we have but still be successful selling to larger companies.

This is where I felt I could make an impact. I thought:

“Don’t mess up the things that are doing really well but help build supplementary process to see success in enterprise sales.”

How to evaluate whether you’re ready to go upmarket

Sam Jacobs: What are the elements that go into evaluating whether you’re ready to go upmarket?

Rick Smolen: I hear all the time, that companies want to move upmarket. The question really is, do you have the value that you give to these larger companies.

Their requirements are significant, the decision-making is a lot more complex. So it all comes down to being able to deliver.

You need to have:

  • The front-end and back-end of your product ready for this new market.
  • A new service model that deliver based on SLAs.
  • The selling muscle to negotiate a deal at a larger company.

Sales process, hiring, and territory management in enterprise sales

Sam Jacobs: What are the different elements that go into upgrading the sales go to market motion so you can tackle enterprise sales?

Rick Smolen: What I did first was to define this new sales process. Then came getting the old sales team to believe they could sell to this new category. Their muscle memory was cut out for high-velocity sales but our new approach involved more meetings and more decision makers.

Common Errors Companies Make as They Go Enterprise

Rick Smolen: We’ve lost a few deals possibly because of the change in mindset that you need to sell in this segment. Common errors I observed were:

  1. The demo was amazing but it was probably done over Zoom or WebEx and not live.
  2. There were a lot of stakeholders involved but not as many touchpoints.
  3. Not making an effort to set up in-person engagement.
  4. No defined process to evaluate RFPs.

What Does a Heavy-Hitting Account Executive’s Profile Look Like?

Sam Jacobs: What do you consider to be the profile of a great AE?

Rick Smolen: It’s an evolving one over time and I might have a hypothesis. For our company, I try to balance hiring someone who has a strong background in talent acquisition software sales with someone with extensive enterprise sales experience.

A requirement for sure is being boardroom ready—can the AE go into an enterprise and build a relationship with an executive there.

Sam Jacobs: How do you test for that?

Rick Smolen: Just the way they speak about a great deal they sold, it becomes evident to me how they think about the value they create. Are they focusing on problem solving or having had an impact on an executive in the company they are selling to.

Another way is to just ask them how they sell to these executives.

Sam Jacobs: What is the right level of experience that you guys need at Greenhouse?

Rick Smolen: From the time I joined, I was hiring both executives and individual contributors. Part of this was for me to learn and part of it was to see what kind of profiles were out there. But what I was most focused on was to see how we could make this work—how we could successfully sell to these larger companies.

I felt I needed to be out there in the field helping our company close deals that could be a game-changer in terms of ARR.

Sam Jacobs: What is the ARR range we’re looking at here?

Rick Smolen: Let’s just say they were well north of a $100K in ARR. Truly a big step-up. So for me, I really felt I needed to believe we could do it.

Metrics and KPIs to Track the Success of an Enterprise Deal

Sam Jacobs: What are the KPIs and metrics you track to know that the deal is having success?

Rick Smolen: We had a big data set of potential targets—a variety of dynamics of whether or not they’d be a good buyer.

Are they forward-thinking with their people organization?

Have they demonstrated that talent is important to their company?
Have they invested in technology?

We’d score a large set of companies like this to be able run ABM (Account Based Marketing) campaigns or segment into territories.

Sam Jacobs: What are some of your favorite ABM initiatives?

Rick Smolen: We created this category called MQA—different from an MQL in the sense that it measures the engagement that an account has with our content before it gets passed on to sales. We’re also using social media and ads, marketing automation, additional touchpoints with the customer based on their engagement with us.

In addition to all of this there’s also an outbound sequence and our existing pipeline.

Overcoming Pricing as an Objection

Sam Jacobs: How do you draw the line on what’s the right amount to quote? Or do you use your seat-based pricing model?

Rick Smolen: The company has a proven pricing model that works. At the same time, part of what makes a great seller, is the ability to have a mutually beneficial negotiation. Joint marketing efforts, events, the service model based on their needs etc.

The key is to create a value based selling mentality—it’s been my #1 goal. Historically, talking about how great the product is never works—it’s all about the problems that the product solves for the customer.

An Impactful Moment in Rick’s Sales Career

Sam Jacobs: When you think about giving advice to folks coming up the ranks, what jumps out?

Rick Smolen: I lived in Asia for over two years—it was an impossible situation with the timezones. I was aware of what time it was in London, New York, and Hong Kong at all times! From that, I came back in an elevated position—getting out of my comfort zone. It was adapt or die. This was like Green Beret training for sales!

How to Get in Touch With Rick

Rick Smolen: LinkedIn works best or at rick@greenhouse.io.

Sam’s Corner

This is Sam’s corner. Another great interview, this time with Rick Smolen—VP of Sales at Greenhouse. They are moving upmarket and it’s a lot harder than it looks. One of the things you’re going to have to redo is your entire sales process. It’s a lot more complex—multiple stakeholders and decision-makers.

  1. Identify these stakeholders and identify their power influence at the organization.
  2. Score their preference and disposition to your solution.

Moving up to the enterprise market is an exciting challenge! This has been Sam’s corner, thanks for listening.

Don’t Miss Episode 06

To check out the show notes, see upcoming guests, and play more episodes from our incredible lineup of sales leaders, visit gtmnow.com/podcast-subscribe

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Finally, a special thanks again to this month’s sponsor, Node. If you want to get in touch with me, find my social handles in my bio below.

I’ll see you next time!

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