Episode OneHundredEightySeven

From Grit to Scale

Guest: Matt Glaser, VP of Sales Operations at Vimeo

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About This Episode

Your first goal should be no surprises.

After that, you’ll learn to pivot from grit to scale.

And along the way, you need to lead for the next generation.

I had a fantastic conversation with Matt Glaser, VP of Sales Operations at Vimeo, about the principles that have shaped his career for success.

“I’m a big believer in education,” Matt said. “It’s helped me stay current and stay sharp.”

Matt shared the 3 overarching lessons he’s learned in his years of experience at different universities, organizations, and businesses.

No surprises

In business and in your career, you have to be prepared. “Surprises can really shake an organization to its core,” he said.

The COVID-19 pandemic is just one extreme example. On a day-to-day basis, Matt pointed out that how you forecast your number is another.

“Being able to predict where your gaps are in your sales funnel is absolutely essential to being able to plan properly,” he said.

If you forecast too low, you blow an opportunity.

Forecast too high, and you’ve overspent.

No surprises also means you do what you say you’re going to do. 

“That permeates through a sales organization, because it really gives others confidence that you’re accountable to your business,” he added.

Matt elaborated on the 4 aspects of his no-surprises mantra.

1. Customer & buyer terms

Ask this: “What do you expect that customer to experience with your company from beginning all the way to the end?” Matt said.

2. Sales methodology

Once you understand the buyer journey, you need to choose the right sales methodology. Not to jam it down anyone’s throat, but to align sales, marketing, and customer success with the same lexicon.

3. Sales funnel

It’s a tall order, but you need to craft a sales funnel that provides the right visibility all the way from top of funnel to middle funnel, to bottom funnel.

4. Tech stack

Obtain tools to help you measure all of the above so that you can both identify and close any gaps — and tighten your predictions.

Matt explained that these 4 aspects don’t necessarily flow in a particular order. 

Each organization should focus on whichever aspect could use the most reinforcement.

From grit to scale

Sometimes companies are in the “roll up your sleeves and get scrappy” mode, while others aspire to scale with repeatable processes.

To Matt, scrappiness and grit tend to be characteristic of companies that are starting off.

Great story of grit: To close a deal, Matt once leapt onto a plane to Arkansas for a Christmas Eve afternoon meeting with a major buying influence. “Had lunch, got back on a plane, closed the biggest deal of my career,” he said.

On the other hand, when you hit volume and complexity, you can’t be flying to Arkansas every holiday. 

“Upper-mid-market to enterprise requires a little bit more planning, more foresight, more cadence, more predictability in what resources you need,” Matt said.

The more things that a sales leader has to coordinate, the more you have to rely on your numbers. “That’s where you need to start scaling because you can’t do it yourself anymore,” he said.

There is a larger community of stakeholders who are all there to help you — if you can explain concretely what you need help with.

Coaching your sales leaders is a major indicator of whether you’re ready to scale.

“To be able to groom the next generation of sales managers, sales leaders have to become coaches,” Matt said.

Which takes time.

Time to coach. Time to work sellers through their pipeline. Time to hone their insights into effective mentorship.

Lead for the future

Remember Matt’s commitment to education? That extends past himself to those on his team.

To partner with sales leaders, he sets up a global infrastructure that enables them to operate. 

“That’s giving them a framework so all the sellers are talking the same language up to the first line managers, the first line managers talking the same language up to the VP, and the VP up to the CRO, and the CRO out of the company,” he explained.

The infrastructure supports what they’re doing with enablement and tech, as well as equips them with a common lexicon.

Reps also need assets that match to where they are in the funnel. A good leader doesn’t make them search for resources themselves but pours information enablement into that role.

  • Don’t inhibit grit. Instead, teach strategies for closing bigger deals.
  • Prepare them for the future. Introduce them to different industries and techniques.
  • Share your network. Bring newer contacts into your spheres of influence.
  • Emphasize learning. A college degree is not the end of your education. Remember that continuous learning starts with modeling a mindset of curiosity and humility.

“Someone like myself has already made a lot of mistakes and has the set of learning from what to do better,” Matt said.

The learning that Matt wants to share with younger sales leaders is this:

Look for feedback, look for knowledge, look for opportunity. Then pursue it.

Between himself and peers he started his career with, Matt said the difference was that he went for the job before he was totally ready for it — and they didn’t.

“Don’t wait for people to come to you and give you an opportunity,” Matt said. “Seek it out.”

For more engaging sales conversations, subscribe to The Sales Engagement Podcast on Apple Podcasts, on Spotify, or on our website.

About The Podcast

The Sales Engagement podcast is the #1 podcast focused on engaging your customers and prospects in the modern sales era. This show features real-life stories and best practices from revenue leaders doing the job day in and day out, in a casual, radio-like talk show.

Each episode features modern tactics, strategies, hacks, and tips to get the most out of your sales engagement strategy and help you navigate the next generation of sales. You’ll find energetic talks that will provide you with real actionable value around building meaningful connections and creating a better selling experience through authentic conversations that you can measure.

The Sales Engagement podcast is here to help B2B sales leaders, customer success leaders, and marketing leaders innovate and usher in the next era of modern sales by building pipeline, up-selling customers, and ultimately generating more revenue with more efficiency.

Hosted by Joe Vignolo, Senior Content Managing Editor at Outreach, and Mark Kosoglow, Vice President of Sales at Outreach.

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