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

6 non-negotiables for me to uncover in every sales cycle.

Without it, you're likely to lose often to 'no decision.'

And no - this is not MEDDIC.


It's the concept of 'why change' and why an investment is required.


1. 𝐈𝐝𝐞𝐧𝐭𝐢𝐟𝐲 𝐚 𝐜𝐨𝐦𝐩𝐚𝐧𝐲-𝐬𝐩𝐞𝐜𝐢𝐟𝐢𝐜 𝐨𝐛𝐣𝐞𝐜𝐭𝐢𝐯𝐞

How to ask:
↳ "Gong aside, what are the top 2-3 strategic priorities you're most focussed on."
↳ "What company-specific objective does Gong align most to, in your eyes?"


2. 𝐀𝐫𝐞𝐚 𝐨𝐟 𝐎𝐩𝐩𝐨𝐫𝐭𝐮𝐧𝐢𝐭𝐲 𝐈𝐝𝐞𝐧𝐭𝐢𝐟𝐢𝐞𝐝 𝐖𝐢𝐭𝐡𝐢𝐧 𝐈𝐭

How to ask:
↳ “For this new launch, through your lenses, what's the biggest single risk to making this a success?”


3. 𝐓𝐡𝐞𝐢𝐫 𝐂𝐮𝐫𝐫𝐞𝐧𝐭 𝐒𝐭𝐚𝐭𝐞

How to ask:
↳ "What metric is that most affecting today?"
↳ "Where is that at today?"


4. 𝐓𝐡𝐞𝐢𝐫 𝐈𝐝𝐞𝐚𝐥 𝐒𝐭𝐚𝐭𝐞

How to ask:
↳ "In an ideal world, where would you want to get that to?"


5. 𝐐𝐮𝐚𝐧𝐭𝐢𝐟𝐲 𝐭𝐡𝐞 𝐑𝐎𝐈

How to ask:
↳ "If you bridged that gap, have you done the math on what that would be worth?


6. 𝐖𝐡𝐚𝐭 𝐭𝐡𝐞𝐲'𝐯𝐞 𝐭𝐫𝐢𝐞𝐝 𝐭𝐨𝐝𝐚𝐲 𝐚𝐧𝐝 𝐰𝐡𝐲 𝐭𝐡𝐚𝐭 𝐝𝐨𝐞𝐬𝐧'𝐭 𝐰𝐨𝐫𝐤.

How to ask:
↳ What have you already done to try and solve that?



Uncover these 6 and stop status quo from eating you alive.

But you won't uncover all 6 of these on the first call

Discovery is a never-ending process

Not just a sales stage


P.S. Closed Won Club is opening back up in  10 days !!! Be on the waitlist for the full discount: https://lnkd.in/gRwyxSti

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

I flipped my discovery approach upside down last year.

Used to show up cold and spend 30 minutes digging for pain.

Now I send proof before we ever talk.

Here's the framework:

"Hey [Name],

Looking forward to our call tomorrow at 2pm.

Quick context that might be helpful - we work with [similar company] and they were dealing with [specific challenge]. Their [title] shared: [concrete quote/outcome].

Thought this might resonate given what you mentioned about [reference their situation].

See you tomorrow! 

[Your name]"


I pull these micro-stories from actual customer evidence.

Not generic case studies. Real quotes, real metrics, real challenges.

UserEvidence makes this stupid easy - I can pull specific customer stories by persona, use case, or industry in about 30 seconds.

𝗪𝗵𝘆 𝗶𝘁 𝘄𝗼𝗿𝗸𝘀:
1. They show up prepared - already thinking about their challenges
2. Disarms skepticism - you've done this before with someone like them
3. Gets them nodding before the call even starts
4. Lowers no-show rates - they're more invested in the conversation


Anyone else warm up prospects before the first call?

Would love to crowdsource other ideas on how 😇

Software stocks just got crushed. $400B wiped out in a week.

ServiceNow down 50% from peaks. Salesforce off 40%. Even Palantir down 30%+ despite crushing numbers.

What happened? New AI models released from Anthropic changed the narrative overnight.

For the first time, investors are asking: "What if AI replaces software altogether?"

Here's the fear: Companies now have three options instead of two:

1. Buy your SaaS software
2. Evaluate 2-3 competitive options
3. Build their own / use AI agents

But here's what most miss:

As a fast growing company, would you rather pay $100K annually for best-in-class software… or divert your finite engineering resources to build, maintain, train on, and secure your own tool. 

Instead of using those engineering resources to focus on your own product/offering.

Similar to COVID, this is a moment where the strongest SaaS companies get stronger, and weaker ones fall off. 

The companies at risk? Simple point solutions with seat-based pricing that's easy to replicate.

It'll be easy to identify the "winners" a few quarters from now. 

Companies that show YoY revenue is accelerating. They are AI beneficiaries . 

Those slowing down? Their stocks will get decimated. And their down fall will become sell fulfilling. 

Exposing which companies actually have a moat, and which were just renting one all along. 


P.S. Think we see this trickle through to the private markets next... funding will dramatically slow for Software companies and "ChatGPT wrappers."

I've spent 2.5 years selling to CRO's and VPs of Sales

If you can't hold your own negotiating, you'll get eaten alive.

Here's my always / never rules for negotiating:

𝐀𝐥𝐰𝐚𝐲𝐬:
-Confirm you are vendor of choice
-Be consultative + work together
-Require a live phone / Zoom conversation
-Still schedule a next meeting after finalizing
-Share levers for better pricing (users, products, longer term, etc.)


𝐍𝐞𝐯𝐞𝐫:
-Negotiate before the 1-yard line
-Try to negotiate over email / text
-Negotiate with a non Decision Maker
-Assume that pricing is the most important
-Use discounting as a crutch for a bad business case



Negotiating is all about learning what's most important to your prospect

That is only learned through strong discovery with the right person

It's not a you vs. them situation 🤝


P.S. Buzzing the 1st masterclass today for Closed Won Club, with Palantir's previous Head of Commercial Sales (ksa) speaking to us... waitlist here for spots in March: https://lnkd.in/gRwyxSti

I’m not sure I would have been successful in 2018 as an SDR if it wasn’t in office. 

Fresh out of college, I had no idea what I was doing. How to open Salesforce, make a dial, what to say, how to handle an objection. 

We learned from screwing up together, laughing, and following each other around when we had one live. 

When we went remote in March 2021, I was pissed. I LOVED being in office. 

A few months later, I LOVED being remote. 

I had an extra 90 minutes. I started working out daily, eating healthier, and got way more done. 

It hit me how much time I was losing between the commute and office chit chat. 

I joined Gong in 2021 in big part because it was remote. I’d never consider mandatory in-person. 


2023 - we opened up a Chicago office for Gong. I went 1-2x a month.

2024 - I started going 2x a week. Was great to see people, grab lunch, and “mix it up.”

2025 - I go every single week. Sometimes once. Sometimes 4x. 

I love hybrid. Never being forced to be in office…

But having that option should you wish. 


Can anyone else not make up their mind between in-person and remote?

Or just keep flip flopping like me? 


P.S. No real point to this post other than sharing things aren’t always black and white. And it’s OK to change your opinion. OG Chicago BrightEdge crew photo below.

Nice guys finish last in sales too.

Being a pushover or a happy ears seller is a good way to get walked all over.

Selling is a 2-way street that is flow of gives/ges.

You have to respect yourself for:
-Your expertise
-Time you prepare for each meeting
-Knowledge in how best to help buyers actually buy
-Time that could be going towards another prospect or customer.

I recently had a prospect go dark for 30 days after committing to an April timeline.

When we got a meeting for early May, most sellers would just be happy they are back online and roll over.

I decided instead to call out the elephant in the room.

A few (real) questions I shared:

“Last time we spoke was April 3rd. We mutually agreed on a timeline to finalize in April and put forward a proposal that reflected that. Why did we not hear from you until early May?”

“Timelines change and we understand that… my ask moving forward is you communicate with us, just as I will with you. Is that a fair ask?”


Respect your time and expertise as a seller.

Because if you do not, no one will.


P.S. Closed Won Club opens up again in <7 days... waitlist just crossed 300+ here: https://lnkd.in/gRwyxSti

Relias team - thank you for inviting me to your Sales Kickoff!

I’ve been lucky enough to work with them for the last 2 years and they are some of the best humans you will meet. 

I got to lead an hour session on leadership deal inspection + coaching. 

And how to leverage amazing platforms like Gong to work smarter, not harder. 

Special thank you to Michael Miller Lara Badanes, MBA Taylor Seus Candace Wallace

Hope to be back in the future for 3 years in a row! :)



 P.S. The healthcare workforce is stretched THIN. That's why 14,000+ healthcare orgs turn to Relias for education, training, and workforce enablement solutions. Awesome people doing amazing things ❤️

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?

One of my favorite workflows right now involves Gong + Clay + Salesforce — and it's solving a problem every sales organization faces. 

Someone new joins a call. They're clearly a stakeholder. Maybe even the economic buyer. And they never make it into Salesforce.

It happens constantly. You want the right contacts attached to your deals. 

Here's the fix:

Gong's SFDC managed package already lets you push new contacts from a call directly into Salesforce. That part alone is huge. 

But here's where Clay takes it to the next level...

Once that contact hits Salesforce, Clay can enrich it. 

Verified email, accurate title, LinkedIn profile, company data — all automatically appended to the record. 

No bad data. No half-filled contact records sitting in your CRM.

Your buying committee is complete. Your data is clean. And you stop losing threads on your most important deals.

If you're running multi-threaded enterprise deals and not using this combo — it's worth 30 minutes of your time to set up.

What's your favorite Clay workflow?


P.S. A new partnership with Clay!!  Will be sharing video content of real Gong + Clay workflows. Excited to share (anonymously) how my most strategic customers are using both together.

In Year 2 of being a solopreneur, I’ve gone back to back on 6 figures in revenue.

Here’s my tech stack as a Creator (in order of cost)...

Digital Consultant
Video Editor
ConvertKit (email list, automations)
Kajabi (Closed Won Club)
Delphi (AI self)
Senja (testimonials)
Pay Kickstart (checkout)
Unbounce (landing pages)
Quickbooks
Zapier 
Wordpress
WP Engine
Video Shoot
Tax Professional
ChatGPT
Claude
ZenBusiness (Annual LLC Filing)
X
Squarespace / Google Domains
Google Workspace
Google Storage


Solopreneur over here - and an army of consultants + tech around me. 

Wild how quickly this list grows 😅 

Any thing I'm missing?

At my last company, we were required to fill out a field “NSTW” prior to every call. 

Hated having to do the admin work. But it trained my brain.
 
NSTW: Next Step to Win

This is your ideal outcome / next step from the conversation, plus 1-2 backup options. 

Now, I do it in every deal in my own notes and add it to a Mutual Success Plan.

I'll jot out all steps we've done so far to show mutual time invested.

Then I'll add the next 2-3 ideal steps in the process.
 

𝗪𝗵𝗲𝗻 𝗜 𝗽𝘂𝗹𝗹 𝘁𝗵𝗶𝘀 𝘂𝗽, 𝗜 𝘀𝗮𝘆: 
"Hey Shane - I spent some time last night building a mutual success plan to keep us fully aligned and wanted to get your thoughts on something if that's cool."
 

Plant this seed at the beginning of your call and come back to it at the end. 

Critical: Do not show more than 2-3 next steps to avoid overwhelming.

It’s a compass for what success looks like, not a full roadmap.


Great backdrop (sharing your screen) for your discovery of their decision process too.

MSP template: https://closedwon.xyz/msp/

Happy Friday all.

taplio

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The Battle

Keith Weightman

Brian LaManna

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