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June 21, 2021
6 min read
Welcome back to The Weekly Pitch for our once-a-week shot of insights and inspiration for the sales community. Eight selling days left to close out Q2! You got this!
Our Feature Story highlights tips from other sales leaders. Influencing your CEO is a neverending journey, but these five relational building blocks lay the groundwork to execute your strategy and vision.
In Leaderboard, we meet Jarron Tate, an experienced sales leader who pivoted from working for a 50,000 employee juggernaut to spearheading sales teams at various startups. His energy is infectious, and he dispenses some fantastic advice for aspiring leaders.
According to Gartner, over half of all Millennials prefer a buying experience free of interacting with sales. While that shrinks to 43% for Gen Xers and 29% for Baby Boomers, it’s an alarming statistic for the B2B sales profession.
The report wasn't all gloomy. When Gartner asked respondents follow-up questions, they found 23% regretted NOT talking to sales during the buying process.
The opportunity for sellers is to make buyers feel more confident in their decisions. The value of the sales rep is preventing this regret.
Most of us have seen data supporting the decline in the average tenure of sales VPs.* It now stands at 19 months. That’s driving more sales leaders to pre-negotiate a severance package before they even start. With less than two years to work with your CEO, on average, we have little time to waste to win over our boss and influence the rest of the organization.
A primer about this list:
Here are five subtle ways to increase your influence with your CEO (or boss):
Communicate over text.
Ideally, you swap casual banter around weekend plans, parenting mishaps, or the latest show you’re streaming. Of course, texting about work stuff is a good sign too, but shoot for a balance. Communicating over different mediums like text humanizes the relationship.
Break bread on the regular.
As society reopens, schedule your recurring one-on-ones outside of the office at a coffee shop or restaurant. Get on a plane if you work in different cities. One leader shared the CEO invites his entire family over for dinner once a month. Socializing outside of the work environment builds a stronger bond.
Start a book club.
Don’t be afraid to initiate, and read a relevant leadership or strategy book where you both find value. Aim for a club of two. It’s not quite the same if your CEO invites you and the entire management team of fifteen to read something together.
Find similar people to admire.
It could be entrepreneurs, industry newsletters, innovators, and influencers you both respect. Landing on a few outside voices helps you coalesce around shared ideas and beliefs to drive the business forward. Solid back-n-forth dialogue is your objective.
Sales leaders often mention a shared activity helps with their overall influence. It could be a hike, a spin class, pick-up basketball, or going on a run together. Breaking a sweat releases those “feel good” endorphins, and again, humanizes the working relationship.
Monitor your heart rate.
Next time you raise a concern or voice dissent with your CEO, note how you feel. Building trust takes time, but you should feel psychological (and physiological) safety after a few healthy bouts of not seeing eye-to-eye. If your heart rate is stable while discussing challenges, and you safely bounce ideas around without getting shut down, you’re probably in a good spot where your voice and influence matter.
This list isn’t foolproof, and it’s worth noting just how hard this is to pull off – personality differences, power dynamics, sales leaders with unrealistic goals, the fact most CEOs have bosses too – the list could go on. But when you exert influence, you’re in a much better position to lead.
Work these tips to gain confidence and get buy-in with your next strategic pivot, change in comp plans, sales org restructure, or request to increase headcount.
Conversely, if none of these ideas are in action, you could still have someone who believes in you. Try these things out to build an even better relationship and influence those around you.
Drop us a line if we missed anything working for you, and we’ll share it in next week’s newsletter!
*Gong published (unsourced) data showing average sales VP tenure declined from 26 months in 2010 to 19 months in 2017. Other published articles offer the same downward trend but were even more outdated. We found no sourced or referenced data behind any of the articles. That said, most sales leaders anecdotally seem to agree with the negative trend line.
As a self-proclaimed retired breakdancer turned HR tech nerd, Jarron Tate seems like a perfect match to head up sales at Roots. The company builds HR plugins right inside one of the biggest workplace communication apps most of us know – Slack. He’s in charge of generating revenue and scaling a sales function for the future. But the startup bug bit Jarron while working at a much more established enterprise.
I worked at a large company and started at the bottom and cut my teeth. I was there for almost 10 years. In that time, I worked with private equity firms to source deals and became drawn to the start-up world, and I have been on that path ever since.
Working for a smaller organization allows him to appreciate the journey a lot more and forces him to stay hyper-focused every day. He likes the balance. When it comes to leadership, you could argue Tate is a natural, and his experience started early:
I have a background in sports and played baseball through college. I started in Junior College and was eventually named captain. Once I went to my four-year college, I was named captain again, so I guess leadership has always felt natural.
What he enjoys most about leadership is the “feeling that comes over you when someone from your team has put in the work to reach an almost impossible milestone.” Tate gets an energy boost from seeing others achieve those next-level goals. He also knows leadership comes back to coaching. Constantly working on the little things leads to significant results in his mind.
His advice to aspiring sales leaders? Set the tone for the team every day by bringing energy and positivity. He also believes future leaders should be comfortable putting people first above all else. If you do that with authenticity, then leading becomes easier. "People will want to work for you." No doubt, if those around you replace "have" with "want," then you're well on your way to leadership.
Jarron doled out more wisdom for The Weekly Pitch.
Your favorite metric to track after revenue is: Pipeline. Without it, there will be no sales.
Shower some praise on a couple of rising stars in the sales world: LJ McIntosh and Elena Pietro are doing great things and will soon be in leadership positions. Their athletic backgrounds and work ethic allow them to consistently overachieve while supporting their teams in any way they can.
If you don’t have this in your sales tech stack, you need to add: Crystal.
This sales or leadership book is a must-read for aspiring leaders: The Energy Bus.
You’re our first leader to choose the “wild card” topic. What else is on your mind? Clubhouse. I think it's a hidden gem. People have conversations daily around issues that have a direct correlation to what you sell.
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