👩🏻‍🏫 Krysten Conner

🚫pipeline anxiety l Terrible dancer l Always a Teacher 🦄🦄🦄 ex Outreach, Salesforce, Tableau 👉🏼👉🏿👉🏽 Click bell/top right to be notified when I post 🔔

You’re not trying to “hit quota.”

You’re trying to become the kind of seller who can repeat top performance across territory changes, market shifts, and new quarters.  

Not with luck. Not with late-quarter heroics. With a *system*.


Most AEs can have a great quarter.  

Consistent top performers have a way of operating that creates sustainable, repeatable results.

That’s what I teach.


I spent 12 years selling Enterprise deals at Salesforce, Tableau, and Outreach. I eventually broke records, 14X’d territory expectations, and ran a 47.6% win rate. But I didn't start that way.

The biggest shift I made wasn’t a new script or a new tech stack.

It was learning how to sell like a top performer actually sells:

✅Reduce confusion (connect the dots, make WIIFM obvious, reduce friction)
✅Run discovery that’s **direct and tactful**
✅Multi-thread early and build real champions 
✅Win the 95% of the sales cycle that happens between meetings
✅Act like a **Sherpa**: guide the buying journey so your buyer never has to guess what’s next


If you’re a rep who’s already performing and you’re thinking:

“I don’t want to be a one-hit wonder.”  

“I want to be on the leaderboard… consistently.”  

“I want make my process sustainable, so my results are sustainable.”

I'm your person.


Here’s what clients say after working together:
 👉 “I closed a $2.66M ARR enterprise deal after 26 months of work, and Krysten's coaching was critical in helping get it across the line."
 👉 "I set an ambitious goal when I started: hit at least 200% of quota in my first full quarter. Working with Krysten helped me turn that goal into reality. I hit 225% and closed the largest deal ever won by a new rep."
👉 "Wanted to thank you and let you know I closed my biggest deal ever in December, $2.2mil TCV, 3 year agreement. We were stuck at one stage with a start date that would have caused the deal to slip from Q4 to Q1, I used your COI principles and in-particular a visual graph that showed what the actual cost was of starting now -vs- later. Ended up getting it done 🤩 Thank you!!"


You don’t need another sales theory.
You need someone who’s been in your shoes - and knows how to win big deals now.

Let’s work together: krystenconner.com


🟢 I offer 1:1 coaching for individual reps, and workshops for sales teams who want to win bigger, faster, and more often.


Browse client wins here: https://www.linkedin.com/in/krystenconner/details/recommendations/



💫"We pay for every lesson with either time or money. And we use the currency we value least."
         -Alex Hormozi

Member

I walked away from the biggest deal of my career. $13.7M. Would've blown my quota out of the water.

But here's what that "loss" taught me...

The CEO had everything: 
✓ A problem we could solve 
✓ Agreement he HAD the problem
✓ Desperate need to fix it 
✓ Budget approved

But one thing kept nagging at me.

Every meeting, he'd ask about customization. 
About "partnering" to build features.
About source code access. 

Classic Build vs. Buy syndrome.

After our 5th in-person meeting (yes, FIVE), I finally saw it clearly.

This wasn't a buyer. This was a builder trapped in a buyer's process.

His personality screamed "I'll do it myself." 
His energy peaked when discussing his team's capabilities.
His questions focused on HOW we built it, not WHAT it could do. 

So I made the call that physically hurt:

I removed it from my pipeline.

My manager: "Are you SURE?" 
My financial plan: "But the commission..." 
My ego: "You're giving up."

Here's what happened next:

→ Freed up 30+ hours that month 
→ Focused on a $1.8M deal that actually wanted to buy 
→ Closed 3 other deals while he was still "evaluating" 
→ Finished with my best year ever

And that CEO? 
18 months later, still building. 
Still solving the same problem.

The real lesson?

Not every deal is YOUR deal.

Some buyers aren't buyers—they're builders in disguise. And the time you waste convincing them is time you could spend closing real deals.

Three questions I now ask myself:

1./ Are they asking about outcomes or architecture?
2./ Do they light up more about building or buying?
3./ Is their real goal independence or results?

If the answers point to "building," I'm out. No matter the size.

Because the best deals aren't always the biggest ones. 
They're the ones that actually close.

What deal have you walked away from that taught you the most?

Krysten Conner

I help AEs win 6-7 figure deals to overachieve quota & maximize their income l ex Salesforce, Outreach, Tableau l Training B2B Sales teams & Individual sellers l 3x Top 100 Most Powerful Women in Sales by Demandbase

Here are the 8 questions CFOs ask before every software purchase. (And they're brutal.)

Every champion I've ever worked with eventually hits a moment of panic:
"What do I say when Finance starts asking the hard questions?"

👉 Most CFOs won't tell you what they're really thinking. They just kill your deal silently.

But I've spent 13 years watching Enterprise deals die in Finance. And I've learned what CFOs actually need to hear.

Here are the 8 questions every CFO is asking behind closed doors, courtesy of the "Only CFOs" newsletter, as highlighted by  Nate Nasralla :

1. Why do we need [X product] now? We were fine before. 
2. What bucket does this fall into, and can you quantify it?
-----Improves efficiencies
-----Increases revenue
-----Mission critical (e.g. cybersecurity)
-----"Candy": nice-to-have tool that doesn't really fit into the above groups 
3. Is the spend in the budget? If not, how will you make up the difference? 
4. How does this tool tie into our company objectives for this year? 
5. What tools do we already have that do something similar? And if similar tools exist, why can't we use those? 
6. Implementation: What are the people / time requirements? 
7. Support costs: Will we need to upgrade soon to enterprise /other tier? 
8. Pricing:
-----If usage-based pricing: I want a detailed analysis on how pricing works and modeling for what our planned usage will look like.
-----If seat-based pricing: I don't want to buy a bunch of extra seats for planned growth. That got a lot of people in trouble when headcount growth halted and layoffs happened.

The deal-killers? Numbers 1, 3, and 5.

At Salesforce, I watched 6-7 figure deals die instantly when the champion couldn't answer those 3 questions clearly.

What are the best way's you've found to prepare your champions for these conversations?

Which of these questions makes your Champions the most nervous? 

PS - Find this helpful? You might like my newsletter. Over 7,000 sellers getting valuable nuggets every week. More details in my bio. Hope to see your name on the list!

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

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

Brian LaManna

"If you keep your nose to the grindstone and work hard and you've got the right people, anything's possible."

You don't have to Google him anymore.

🌹 Rose Bowl
🍑 Peach Bowl
🏆 National Champions.

I debated whether or not to go to the last game. Grateful for the people that pushed me to 'take the trip.'

Will forever be one of the most special times in my life. 

We work to live, not live to work. 

Hoo Hoo Hoosiers!!! 🥹

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

Until further notice, this is an IU Football + Mendoza fan account.

We are here in Miami and ready for the National Championship.

I have never anticipated a game more in my life.

Full butterflies. Pit in my stomach.

But confident as ever.

Predictions?


P.S. No matter how it ends… I’m sad this season will be over. A magical run and some of the most fun I’ve had traveling + reuniting with college friends. But we don’t go to war with warm milk & cookies. Time to win.

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I now have 12 free resources built for 2026, all of them below.


𝟭. 𝗔𝗰𝗰𝗼𝘂𝗻𝘁 𝗣𝗹𝗮𝗻𝗻𝗶𝗻𝗴 𝗧𝗲𝗺𝗽𝗹𝗮𝘁𝗲 - Organized way to keep track of all your prospecting efforts and people you're going after.

https://lnkd.in/gwjX9Nya


𝟮. 𝗦𝗮𝗮𝗦 𝗔𝗰𝗿𝗼𝗻𝘆𝗺 𝗚𝘂𝗶𝗱𝗲 - Terms I never knew existed until I got into tech sales. 

https://lnkd.in/g9R9WH53


𝟯. 𝗠𝘂𝘁𝘂𝗮𝗹 𝗦𝘂𝗰𝗰𝗲𝘀𝘀 𝗣𝗹𝗮𝗻 - Template to keep you and your champion fully aligned through a deal cycle. Also, helpful to navigate security, legal, and who the signer ends up being.


https://closedwon.xyz/msp/


𝟰. 𝗙𝗶𝗿𝘀𝘁 𝗖𝗮𝗹𝗹 𝗗𝗶𝘀𝗰𝗼𝘃𝗲𝗿𝘆 𝗙𝗹𝗼𝘄 - Top 12 discovery questions to follow a typical first call flow.

https://lnkd.in/g75tkxRM


𝟱. 𝗗𝗲𝗺𝗼 𝗔𝗴𝗲𝗻𝗱𝗮 𝗦𝗹𝗶𝗱𝗲 - Agenda slide to cut the 2 minutes and show a visual instead. Buyers love visuals. This is it.

https://lnkd.in/gD5vaXf7


𝟲. 𝗦𝗮𝗹𝗲𝘀 𝗥𝗲𝘀𝘂𝗺𝗲 𝗧𝗲𝗺𝗽𝗹𝗮𝘁𝗲 - Grab a Google Doc template of my exact resume. 2 pages on other best practices, tips, and dos/don'ts.

https://lnkd.in/gESuWPBW


7. 𝗖𝗼𝗹𝗱 𝗖𝗮𝗹𝗹 𝗢𝗽𝗲𝗻𝗲𝗿𝘀 - 8 proven openers to get the call started hot.

https://lnkd.in/gdPP_D8J


8. 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿 - Actionable sales tips (and some B+ memes) delivered to your inbox every Monday. Trusted by 11,200+ sellers and counting. Read in 2-3 min.

https://lnkd.in/gjeVd_U8


𝟵.  𝗢𝗯𝗷𝗲𝗰𝘁𝗶𝗼𝗻 𝗛𝗮𝗻𝗱𝗹𝗶𝗻𝗴 𝗚𝘂𝗶𝗱𝗲 - Quick reverses for the most common objections and methodology on how to 'handle' them.

https://lnkd.in/g36efdAw


10. 𝗔𝗹𝗹 𝗼𝘁𝗵𝗲𝗿 𝗿𝗲𝘀𝗼𝘂𝗿𝗰𝗲𝘀 on Closed Won.

https://lnkd.in/gVY8Xpxc


♻️ Please consider resharing if it'd help others in your network.

📌 Sellers - what (free) resource should I build up next?

Joined Gong in 2021 to sell a -hot- product that (it felt like) everyone already knew. Then June 2023 happened...

We launched Gong Engage with 0 customers.

Suddenly, I wasn't selling just the #1 conversation intelligence platform anymore. 

I was selling an unproven sales engagement tool in a crowded market.

Here's the problem we hit immediately:

Every prospect asked: "Who else is using this?"

We had no case studies. Very few Beta references.

And burning through our early adopters on every single deal? 

Not sustainable when you're trying to get to 1,000+ customers fast.

That's when we started using UserEvidence.

Instead of manually tracking down customers for references, UserEvidence automatically captures product reviews, pulls verified stats, and creates battle cards we can actually use.

Now when a prospect asks "who else uses Engage?" - I can instantly share:
* Real customer quotes
* Specific use cases
* ROI metrics from similar companies

No begging customers for time. No stale case studies from 6 months ago.

As we've grown into a true multi-product platform, UserEvidence has become essential. 

Different products, different personas, different proof points - all organized and accessible.

If you're scaling a new product or expanding your platform, you need proof at scale.

Give UserEvidence a look: https://userevidence.com/


P.S. Will be partnering with them closely in 2025 to share other ways I am leveraging them. Thanks all for the support!

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

Tell tale sign of junior sellers is trying to avoid risk in their deals. 

And getting defensive about risk in forecast / pipeline reviews.

Risk is uncomfortable and junior sellers often try to ignore it and 'hope' that it doesn’t come to fruition. 

When in reality the opposite is best.

Get comfortable knowing risk exists in every deal and it doesn't mean it's your 'fault.'


I write out the biggest reasons why I will lose the deal. 

Then 'the action' of how I will get in front of it.

Here’s a (real) scenario of a deal I had earlier this year:
-12 month evaluation and we were named vendor of choice. Fit perfectly to their initiatives. Great critical event with a competitor renewal in 2 months but we aren’t speaking directly with the decision maker on it (CRO). Have 5+ champions advocating for us.

What most sellers would think:
- Wow, we are in a really strong spot! We have so many champions and fit perfectly with their goals. Bummer the CRO isn’t more directly involved but my champ will get it done.


Here’s how I’d approach it instead.

Risk:
- Work/effort to migrate over to a new platform
- CRO not having direct involvement
- Their current vendor will try to save this renewal with aggressive pricing.
 
Action:
- Call out the risk of both next call
- Recommend a 30 min call with implementation to discuss migration
- Recommend a 2nd, 30 min call with CRO and main POC to review one-pager exec business case we will build for them.


For any fans of the book 'The Obstacle is the Way.'

'The risk is the way' in your deals cycles.

Don't avoid it, go through it.


P.S. Closed Won Club goes live 1/26. Be the first to hear about it here: https://closedwon.xyz/

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Brian LaManna

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Engagements

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