RVP, Sales @ Bullhorn - I talk about creating systems for sellers to scale your impact, not your hours

3 years ago, I was drowning...

As an RVP at a fast-growing tech company, my life had become an endless stream of:

• "Urgent" emails
• Back-to-back meetings
• And constant fire-fighting

Waking up early and working late into the night.

My phone was always buzzing with notifications.

To make matters worse, it was taking a toll on my family.

The breaking point:

Missing my son's jujitsu belt test.

Something I'd promised I wouldn't do.

That night, seeing the disappointment in his eyes, I knew something had to change.

I spent the next year obsessively learning, developing & testing different productivity systems that would allow me to:

• Still perform at a high level
• Stop feeling perpetually overwhelmed
• End working nights/weekends just to keep up

I started creating what I called "mini-systems"

Small changes that had a compounding effect.

What began as a quest to regain control of my calendar...

Evolved into an operating system that helped me recover 10+ hours every week.

More importantly, spend more time w/ family. 

I've started documenting my learnings & "mini-systems" and now share them with others through my content and weekly newsletter The Systematic Sales Leader.

My goal is to help as many sales leaders as possible avoid the same burnout I and so many others experience through tested and proven systems.

If you're curious to learn more, check my "featured section" for a few free resources.

Keith Weightman

AE @ Gong | Closed Won 🦙 | 5x President's Club

Creating raving fans @ Gong. Founder of Closed Won. Dad to Monty 🐾 

Brian LaManna

Seeing my name on a NY Times Square billboard is not something I had on my 2026 bingo card... but nor was baby monkey Punch... so here we are. 

Huge thank you to the team at trumpet 🎺 for making that happen.

(The NY Times Square billboard... in case that needs clarifying)

Beyond the surreal moment, I want to give them a genuine shoutout for what they actually helped me accomplish this year.

I used Trumpet in every single enterprise deal I ran. Every one. Deal rooms became a core part of how I sell.

The results backed it up:
-Win rate went up
-Sales cycles got shorter
-Average sale price grew

That's the trifecta. 

And a big piece of that came down to having a professional, organized space where buyers could engage, internal champions could sell on my behalf, and nothing got lost in a 47-message email chain.

2025 was a proud blowout year for me, and Trumpet was part of that story. 

Grateful for platforms that actually move the needle.

Thanks, Trumpet 🎺

Brand partnership • AE @ Gong | Closed Won 🦙 | 7x President’s Club

Most painful (lost) deals I remember.

-One that had a DocuSign out for signature around March 15th, 2020. The team took a few extra days to look it over... COVID hit... and they never ended up signing.

-6 month evaluation, decided they were going to move to us from a larger competitor, and then not realizing they had an auto-renewal. I take fault for not pressing harder on this.

-21 month deal cycle that continued to push quarter after quarter for a variety of excuses, despite promising interest. Nothing as painful as a super long deal cycle with twists and turns. Eventually turned it Closed Lost.

-Running a successful evaluation with someone who told me "I am the decision maker and signer on this" ... when it came to sign, someone else blocked it from happening. Lesson learned... if someone blurts out "I am the decision maker" .... they are most definitely not the decision maker 🤣


Quickly learned to never celebrate a deal until it's signed.

Time really does kill deals sometimes.


P.S. Redesigned the website around Closed Won Club at https://closedwon.xyz/ ... how do we like it?

AE @ Gong | Closed Won 🦙 | 7x President’s Club

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The Battle

Keith Weightman

Brian LaManna

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Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Keith Weightman's LinkedIn Performance

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Performance ScoreKeith Weightman's LinkedIn Performance