Go-to-market mavericks: Michael Sharp on exec cold calls, business acumen, and more [video]

We recently talked to Michael Sharp, Senior Vice President of Commercial Sales at Pluralsight, about sharpening your sales skillset as part of our recent event: Future-proof your sales career.

Here are three of the top takeaways from that conversation (check out the full recording above).

1. Think like a prospect

Michael started his sales career in the deep end: cold calling C-level executives at Fortune 500 companies.

It taught him the value of research, preparation, and, arguably most important, empathy.

“The reality is any CxO that you're selling to is working on behalf of the vision and the goals that the CEO has set forth for that organization,” Michael said. “Their function that they manage has a critical role in bringing that vision to life or helping the business achieve that particular target. And so, think critically around, like, who is the CEO? What is the vision for the business the CEO has laid out?”

Whether you’re selling to the C-suite or an end user, it pays to put yourself in the shoes of your prospect and develop a deep understanding of their goals, challenges, and priorities.

It’s sales strategy 101: Get a grip on your prospect’s function at their company, form a hypothesis around the challenges that they may be facing, and build a business case for how your product can help.

The hard part is collecting, synthesizing, and taking action on this information quickly and at scale. Luckily, today’s reps have tools—up to and including AI agents—that can help with the heavy lifting.

“I would leverage a lot of the tools and resources at your disposal,” Michael said. “We are so fortunate today that we have a lot of AI tools that can help connect our company's value proposition to any company's industry or even that unique business and what that company has said out there in the media about their organization.”

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2. Lean on your team

Business acumen—that is, the knowledge that helps reps understand and navigate different prospects’ business situations—typically comes from experience.

But that’s not much help to reps early in their career. They haven’t talked to executives day in and day out about their industries, companies, and strategies.

It’s in these cases where reps should lean on their managers, teammates, and peers.

“It's funny, as a sales leader, we tend to get pulled in at the end of a sales process as if we have some magical closing wand, right?” Michael said. “But oftentimes earlier on is where we can be most helpful shaping that sales process.”

Sales leadership, enablement, product marketing—odds are there are people at your organization who can help you fine-tune your approach to research and messaging.

It’s also worth looking outside your company to develop your skills.

“If you go on LinkedIn today, there's a ton of high-quality perspective and content out there on a daily basis,” Michael said. “Just finding those thought leaders that exist out there, finding the companies that you think are doing really innovative things, following them and consuming their thought leadership, consuming their research, engaging with those influencers, I think really is an easy way to just build your knowledge of what modern sales skills are working today.”

As far as prioritizing professional development within a company, Michael is a big believer in managing up.

“I think a seller superpower is to manage your manager to develop you,” Michael said. “Be relentless with your direct manager around what skill gap, what capability they think, if you could improve a little bit [...] would be a game changer for your performance. Do not wait for them to come to you and to provide you with that perspective. Run to them. Be relentless about asking those kinds of questions. They're going to be your most incredible resource to fast cycle your growth and your development.”

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3. Measure wisely (and collaboratively)

Michael is a self-proclaimed “data geek,” but he also believes that data without discipline can do more harm than good.

“There's this saying: You can't manage what you don't measure, but don't measure what you're not planning on managing,” Michael said. “And I like that a lot because I also think folks can go to the other end of the spectrum and just get totally overwhelmed with data points and with dashboards.”

His advice? Focus on your ultimate target metric and then zero in on the metrics below that act as leading indicators.

“You can drill down even deeper, but I call that second layer the metrics that matter,” Michael said.

For example, if pipeline generation is your key metric, the metrics below might relate to source attribution, speed to lead, and conversion rates.

Once you have a handle on which metrics matter most, it’s essential to make sure all go-to-market teams are singing from the same sheet of music.

“The most common issues that I see are [...] point dashboards,” Michael said. “We have this dashboard that looks at this outcome. We have marketing over here, and they look at marketing performance in this way. And I think that's a symptom of each business unit or each organization or each function reporting on their own performance and their own success and losing sight of that more holistic model.”

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These are just some of the takeaways from our conversation with Michael Sharp.

Watch the recording for the full story.

And stay tuned for the next edition of Go-to-market mavericks!

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