Stop chasing everyone.
Build the point of view, creative outreach, and follow-up system that make the right buyers want to talk to you.
You are the last moat.
In a market where everyone has the same tools, your voice, judgment, and point of view are the advantage. The way to win isn’t to sound more polished. It’s to become more unmistakably yourself.
How we can work together
Make the next conversation count.
Coaching and strategic support for employee benefits sellers, teams, and leaders who want clearer thinking, stronger conversations, and consistent execution.
1:1 Sales Coaching
Direct, practical coaching for benefits sellers who want a stronger point of view, more creative ways into the right accounts, and a follow-up motion they can run consistently. The work is built around Sims’s proprietary 4E framework.
- Weekly coaching sessions
- Lead-list + pipeline review
- Creative drops + direct mail
- Personalized sequences
- 4E framework application
- Weekday text and email access
Team Coaching
Start with a focused workshop, then turn the ideas into habits through an ongoing coaching rhythm built around the team’s real work.
- Hands-on team workshop
- Content pillars
- Post examples
- Outreach guides
- Daily activity plan
- Weekly office hours + script feedback
Project Engagements
Focused strategic work for benefits companies that need an experienced operator to help move a defined revenue initiative from idea to execution.
- Offer development
- Sales narrative
- Positioning + messaging
- Broker activation programs
- Go-to-market sprints
- Messaging for vendor partnerships
In their words
Less noise. Better conversations.
The work is practical by design: clearer thinking, repeatable behaviors, and results clients can feel in the field.
“I’m consistently booking 2–3 meetings per day through LinkedIn, but more importantly, those conversations feel aligned. I’m attracting the right people instead of chasing everyone. Sims doesn’t teach you how to push harder. He teaches you how to show up better.”
“In this day and age, you can make 10,000 calls and get nothing out of it—I’ve done it. He teaches you to break through that noise so you don’t have to make 10,000 calls.”
Riley SchleiferAdvisor, Hodge, Hart & Schleifer“I believe in social selling. Getting a room full of salespeople to actually believe it and use it is another thing entirely. Sims made that happen. Our enterprise team used what they learned to book a meeting with a multi-billion dollar prospect. When my consultant relations team uses these tactics, they book a meeting with a top-tier broker about once a week.”
Amanda VolnerHead of Sales, Healthee“The 1:1 coaching time I had with him was invaluable. We discussed things as simple as foundational concepts like time blocking for prospecting and outreach to advanced multi step touch points and custom messaging. I never expected my LinkedIn posts to get me inbound leads but here we are. Thanks, Sims!”
Ashley McQuadeSenior Account Executive, Thatch“His expertise and guidance have been invaluable in helping me fill my pipeline, set more calls, and ultimately work with more ideal clients. Thanks to Sims, I’ve seen a significant improvement in my company’s results.”
Sarah BordersCo-Founder, Benefits Compliance SolutionsSims Tillirson has spent more than a decade inside employee benefits—across sales, partnerships, and go-to-market strategy.
He’s worked with insurance carriers, enrollment firms, and benefits technology companies ranging from pre-seed startups to Fortune 1000 organizations. That range gives him a clear view of what buyers respond to, where revenue teams get stuck, and how to turn a strategy into behavior.
His work centers on creating and operationalizing new offers, building broker partnerships, and giving teams a go-to-market motion they can actually sustain.
Outside of the work, he’s a recording artist, multi-instrumentalist, singer-songwriter, tattoo enthusiast, and NASM-certified mental fitness coach.
Ready to be easier to buy from?
Start with the challenge in front of you: an individual sales motion, a team that needs a coaching rhythm, or a strategic project that needs an experienced operator.
Jam with me
