👩🏻‍🏫 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!

Founder @ FDTC → I help startups go from $100K-$15M by improving sales processes, playbooks, & people → Building the #1 SaaS sales coaching program for AEs → Featured in Techstars & Sales Hacker → #helpmedontsellme

It was Monday morning, 11 AM when I went to my boss and said, “I’m sorry, this job, sales...it’s not for me” and I left.

That was 13+ years ago.

At 22 years old I landed my first real job fresh out of college ready to be a “career person.”

I crushed the interview.

But when I came into work for my first day at 10am, I quickly realized that I was scared sh**less of sales, and quit within the first hour.

For the next 3 years, I had PTSD and avoided sales like the plague.

I played it safe and stayed in my comfort zone.

No sales-related stuff whatsoever.

I lost my confidence and ambition. 

I missed career opportunities and wasted away my early 20s.

Fast forward to present day:

I'm a former 2X VP of Sales who took 1 startup from $0 ARR to ≈ $10M ARR in 4 years, and another from $1.5M to ≈ $4.6M ARR in 18 months.

I now teaching SMB AEs and teams how to be top sellers, make higher 6-figures, and get promoted through repeatable systems and playbooks.


Want to learn more? Book a clarity call: https://calendly.com/fdtc/30min 


P.S.⚠️ Grab my top (FREE) 24 discovery questions 6,000+ salespeople are using: https://bit.ly/4d3B2sl


Otherwise, you can find me here:
► YouTube: https://www.youtube.com/@demotoclose
► iTunes: https://apple.co/3Fome9g | Spotify: https://spoti.fi/408V0LS
► Twitter: https://twitter.com/@mistamor

Mor Assouline

A CRO of a Series B company DM’d me this a few days ago:

“Every single AE hit quota this month. 14 for 14. Not only has this never happened before at our company, I’ve never seen this happen at any company I’ve worked at.”

This wasn’t luck.

I’ve been coaching their AEs for the past couple of months.

→ 1:1 sessions.
→ Real call reviews.
→ Deal reviews and planning.
→ Mindset / Belief upgrades.
→ Building better processes and playbooks.
→ Working alongside their talented sales managers every week (who are absolute rock stars)

Here’s what we cleaned up:
1. Rebuilt how they run discovery calls for different segments / personas.
2. Rebuilt how they run demos so they’re selling the problem, not the product.
3. Coached them on how to hold the line when going over pricing.
4. Trained them on how they manage their time and pipeline.
5. Each AE had a personalized skill plan that we reviewed every week and tracked progress.

Every single rep leveled up, and it’s been working.

The sales team set the record for the most new ARR in their company’s history, and this is just the beginning.

You know what's more expensive than coaching?

Replacing reps every six months because they never had a real process to follow.

Missing your number three quarters in a row while you "figure it out."

Watching your best people leave because they're tired ofcarrying the team.

14 for 14 is cheaper.

Founder @ Demo to Close / The #1 Sales trainer & coach for SMB AEs and SaaS companies that want to sell better & close larger deals / 2X VP of Sales / Unseller

I coach an SMB AE who's hit $15K months in commission alone 3 quarters in a row. Within 1 year, he got promoted to MM. Here's something he does that many reps aren't willing to do:

→ He isn’t scared to surface objections on calls.

Most AEs try to avoid objections, but he proactively looks for them.

His thinking: I rather be on the call handling concerns that would come up when we hang up

Some examples I taught him to ask:

→ After showing a feature: “Based on how we [solve problem] what do you feel might not work for you or your team?”

→ At the end of the call: “When you take this back to [stakeholder], what would some things they’d have reservations about that would pause all this?”

→ During call: “What other initiatives is [higher stakeholder] dealing with that would cause this to be pushed to next quarter?”


The top 1% of AEs are masters of asking great / thought provoking discovery questions.



P.S. Here are 24 more discovery questions 6.6K+ AEs are mastering: https://lnkd.in/eR69raD4

High-paid SMB AEs spend their time:

→ Planning their day the night before
→ Recharging so they don’t burn out
→ Disqualifying opps that are not a fit
→ Upgrading their mindset, beliefs and skills
→ Reviewing their metrics weekly like a CFO
→ Calling buyers as soon as they fill out the form
→ Disqualifying fast to protect their time and calendar
→ Consistently blocking out time to prospect and doing it


Low-paid SMB AEs spend their time:

→ Pitching during discovery
→ Letting their calendar run them
→ Waiting for marketing to send them leads
→ Following up with “just checking in” emails
→ Arguing with RevOps about Salesforce stages
→ Complaining about quota instead of raising their skills
→ Talking about features instead of problems on discos/demos
→ Hoping this quarter will be different without changing anything

Same seat.

Different mindset.

Different habits.

Different skills.

taplio

The Battle

👩🏻‍🏫 Krysten Conner

Mor Assouline

Followers

Posts

Engagements

Likes

Performance Score👩🏻‍🏫 Krysten Conner's LinkedIn Performance

Performance ScoreMor Assouline's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

👩🏻‍🏫 Krysten Conner

Mor Assouline

Followers

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);}👩🏻‍🏫 Krysten Conner's LinkedIn Performance

Performance ScoreMor Assouline's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance Score👩🏻‍🏫 Krysten Conner's LinkedIn Performance