👩🏻‍🏫 Krysten Conner

krystenconner.com

--> Pressure to hit your number got you lying awake at 2:41am?
--> Stressing over deals that are ghosting or slipping?
--> Burned out & feeling major anxiety?

Empowering tech sellers to close more complex deals is what drives me.

I spent 12 years in Enterprise sales as an Account Executive with multi-billion dollar tech companies like Salesforce, Tableau and Outreach. Along the way, I blew past performance goals in multiple roles.  Doing 14X what anyone had done in my territory, being #1 in new logo acquisition, and achieving a 47.6% win rate.

It wasn't always like that, though.

Early on, I couldn’t confidently qualify deals in or out quickly. I wasted lots of time on deals that didn't turn out to be real. My discovery felt haphazard, and I struggled to get prospects to go in depth or quantify their pain.

My first sales cycles were some of the longest on the team. Deals frequently slipped, and I got ghosted a lot. All which I felt powerless to change. I was always waiting for the customer. I didn’t know how to lead so buyers wanted to follow.

You might relate to feeling like I did: burnt out, anxious, and like you don't belong in sales. The sad part is feeling behind, scattered, and overwhelmed has become the new norm.

It took me over 10 years to gain the confidence, knowledge and skills that I needed to be a consistent top performer.

My mission is to ensure you get there faster - by sharing what I’ve discovered throughout my 12-year career.

My content and training has been featured by: 
--> pclub / Chris Orlob
--> 30 Minutes to President's Club
--> Kevin Dorsey / Live Better, Sell Better
--> Sell Better / Daily Sales Show
--> Outbound Squad
--> Challenger
--> Vidyard
--> RepVue

Here’s what my clients say: https://www.linkedin.com/in/krystenconner/details/recommendations/

--> Sign up for my newsletter for weekly coaching in your inbox:    krystenconner.com
--> Schedule a consult here:   https://scheduler.zoom.us/krysten_conner/coaching-consult

I help AEs win 6-7 figure deals to overachieve quota & maximize their income

pclub.io

Multi-thread Your Way to 34% Higher Win Rates 
Access multiple Decision Makers faster with proven templates & approaches
Expand your footprint and get "high and wide" access to multiple influencers in your top deals.

Sign up for the Multi-threading Masterclass here!

Course Author:  Multi-Threading Masterclass

Outbound Squad

Helping you pack your pipeline with qualified meetings.  Especially those shiny new logos.

Coach

Outreach

• 10-27% more revenue (Forrester study)
• 31% more meetings booked
• 29% more opportunities

Outreach is like Amazon for sales activities.  Makes everything about it faster & easier, more trackable, and you get better info for better decisions.  Frees you from mundane work. So you can do revenue generating work.

But don't take our word for it.  Adobe, Tableau, Zoom and 5,000+ other clients get extraordinary results with Outreach's system of action. Salesforce, Microsoft and SAP have all invested millions in Outreach.

Honeywell, Cisco and SAP drive predictable and measurable growth, increase efficiency + effectiveness of all customer-facing teams, and improve visibility into sales activity and performance with Outreach.

Enterprise+ Account Executive

Outreach:
• Forbes Cloud 100 for 2018-2020
• #1 in G2's Best Products for Sales, 2020
• $4.4B valued "Unicorn" 

Hustle + grit, being a decent human, and helping clients get what they needed were my 'few & vital'
 
Led to these results:
• #1 on my team and #3 in all of Enterprise for New Logo acquisition
• 711.21% YoY ARR growth in my book - all New Logo
• Top 3 rep in East region for new ARR, with 47.6% win rate 

Outreach optimizes every touch throughout the customer journey, managing interactions across email, voice and social.  Machine learning guides sales and service teams to take the next right actions.

Headquartered in Seattle but with offices in San Francisco, Tampa, and London, Outreach has received $289M+ in funding from top tier investors. **Backed by Salesforce & Microsoft** as well as Lone Pine, Meritech, Spark, DFJ Growth, Sapphire, Trinity, Floodgate, Mayfield, Premji Invest, Steadfast Capital Ventures, Sequoia Capital, Tiger Global Management Vista Equity Partners, Microsoft, SAP and Salesforce Ventures

Enterprise Account Executive

Tableau Software

How do you actually accomplish digital transformation, in real life? How have others built a data culture? What have they gained as a result of all that time and effort?

Working with clients to answer these questions helped me achieve: 
• 137.73% YoY growth in my book - this put me in the Top 7%; #5 out of 63 reps
• 145.36% of Services quota; #22 out of 63
•  41% partner attachment (sales is a Team Sport)
• The honor of presenting to my peers on Prospecting at GSKO 2020

Enterprise Accounts, Financial Services

PowerSchool

PowerSchool creates tech that makes it easier, faster, and more cost-effective for schools to find and
keep great teachers. As a former teacher, this was a purpose close to my heart.

In this role, I worked with large school districts and associations (5,000 - 50,000 employees) across
5 states. This included all stages of the sales cycle: market development, new business sales and
expansions.

• Truly partnering with the districts I served allowed me to achieve an average of 127% of my revenue goals every quarter.  
• This partnership approach also helped me do 14X what prior reps had done in the same geographic territory.
• Over 61% of my clients had never worked with us before.  Earning their trust was an honor.

Strategic Accounts

Hello Alice

Super pumped about getting my side hustle accepted into this national accelerator.  Circular Board was the Start-Up Accelerator that launched Hello Alice.

Founder - Member of Fall 2016 Founders Cohort

Haas & Wilkerson Insurance

Haas & Wilkerson is one of the nation's largest privately held insurance brokers.  I worked as a Risk Consultant partner for high attendance entertainment events across the country. 

• Created Challenger Sale strategy for National Accounts division (slide deck below)
• Sales and Business development for National Accounts division, both for-profit and nonprofit
• Strategic Sales Partnerships project team

Strategic Account Executive (Field)

My clients were all small/medium businesses and nonprofits, run by folks driven to pursue their dreams, passions and callings.  It was a thrill to develop creative solutions for their organizations.  

While the numbers alone can never tell the whole story, they do help quantify impact:
• Sales, new business development and client retention, as well as growth and operations strategies for our agency’s fastest growing unit (growth rate of 21% during my tenure)
• Created improved work processes that cleared 5 months of backlog within 8 weeks
• Introduced pilot program that increased efficiency of analysis process by 48%

Business Unit Manager - Select Accounts

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

Feel like you're trying to do everything right… but deals keep slipping, ghosting, or dragging out forever?
You’re not alone.

Enterprise sales is full of hidden traps no one warns you about:
 ❌ Deals that seem real but never close
 ❌ Discovery calls that stay surface-level
 ❌ No clear way to qualify quickly—or confidently
 ❌ “Great calls” that vanish into silence
 ❌ A cycle that feels out of your control

And somehow, you’re still expected to hit an aggressive number.
In a tough market. With no real playbook.

It’s exhausting—and it’s not your fault.


The worst part? You don’t feel in control.
You’re anxious. Burnt out.
And starting to wonder if you're even cut out for this.

But it’s not you.
You were just never taught how Enterprise sales actually works.


What if you didn’t have to figure it out the hard way?


I spent 12 years selling Enterprise deals at Salesforce, Tableau, and Outreach. I hit 47.6% win rates, broke records, and 14X’d territory expectations—but it didn’t start that way.

Early in my career, I felt stuck and scattered too. I had to teach myself how to run deals with structure, control, and confidence—because no one else was doing that kind of coaching.


Now, I teach you the strategies I wish I had sooner:
 ✅ Run Discovery that actually drives urgency
 ✅ Qualify fast—without sounding like a jerk
 ✅ Multi-thread without being annoying
 ✅ Speak the language of Executives
 ✅ Lead deals so buyers want to follow


Here’s what clients say after working together:
 👉 “Went from 2% of my number to 106%”
 👉 “Helped me close a deal with a $5B account - that 2 of my predecessors failed to close.”
 👉 “I closed the largest contract in my company’s history from prospecting to close because I implemented in real time what she taught me.“


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


Want to sell like a top performer—without waiting 10 years to figure it out?
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

After 7+ years in Enterprise sales, these are the 5 questions I ask Executives on deals that keep pushing out. 
 
They help me figure out which deals are might be delayed vs. deals that are dying☠️ 
 
There are 5 different areas. And the last one is the most important at EOY.
 
 
Here are the 5 questions: 
 
 
💰1) CONTEXT 
"We were originally working to get this started in Q1. Sounds like this now might be a Q2 thing. 𝗜𝘀 𝘁𝗵𝗮𝘁 𝗱𝘂𝗲 𝘁𝗼 𝗕𝘂𝗱𝗴𝗲𝘁, 𝗕𝗮𝗻𝗱𝘄𝗶𝗱𝘁𝗵 - 𝗼𝗿 𝗯𝗼𝘁𝗵?" 
 
Follow ups: 
 
"Ok got it. What changes in Q2?" 
 
"Has Q2 budget been earmarked already?" 
 
"Curious - what else is being implemented Q2?" 
 
 
 
📊2) PRIORITIES 
"Is there a specific goal or initiative in Q1-Q2 this aligns with?" 
 
 
 
🤔3) TIMING 
"November/December is often when Executives finalize goals for the next year. How are you feeling about your upcoming targets related to [problem I solve]?" 
 
 
 
💥4) IMPACT 
"Based on your current & future targets, when would you need to see an impact from something like [my product]?" 
 
 
 
❓5) PROCESS 
"How long did it take to get through Legal the last time you bought software? How about Security? Based on those experiences, do we think a Q4 timeline is even possible? Or is this more likely a Q1 thing?" 
 
 
 
If they can't (or won't) go into specifics, the deal is probably dying 😭 
 
There is an inverse relationship between vague answers 
 
& deals that close🕵️‍♀️🔍 
 
 

What are your favorite questions to figure out which deals are coming in vs. dying out?

Talks about #sales, #saassales, #pipelineanxiety, #salesenablement, and #salesdevelopment

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

How you know it's an Enterprise sale: 
 
- The deal dies 3 times before it's signed 
- 9 months seems like a very short deal cycle 
- Root canals are more enjoyable than the InfoSec review 
- You know more about what's happening in other depts than the Champion does 
- When it's finally signed, you are simultaneously relieved, elated and exhausted 
 
 
What did I miss?

I help AEs win 6-7 figure deals to overachieve quota & maximize their income l ex Salesforce, Outreach, Tableau l Founder, Enterprise Sales Accelerator l Training B2B Sales teams & Individual sellers

I recently talked with a VP of Sales hiring for 3 open AE roles. My jaw fell open when he told me what most candidates *don't** do. In under 1 minute, he told me 4 things that average sellers aren't doing when they apply. 
 
--> The good news is, you can do them all in under 15 minutes. 
 
 
Here's what he said about typical AE candidates: 
  
--> "They don't call or email me or my team." 
 
--> "They don't connect or message me on LinkedIn." 
 
--> "They don't ask any questions (aka no Discovery)." 
 
--> "They don't follow up on phone screenings, mentioning specific takeaways." 
 
 
 
But the candidates that stood out...Here's what they did instead. (And these are actual IRL candidates, btw.) Here are the VP's word for word quotes: 
  
--> "She asked about my priorities. I gave her all the answers! I'm an open book." 
 
--> "She sent me a note after our screening call. We only talked for 15 min, but she remembered 2 key points." 
 
--> "He called me to follow up. He called my team to see what it was like working with me. He had a POV on why he'd be a fit."** 
 
 **important note here: This candidate scored a 'maybe' on the sales skills assessment. But this call earned him a 2nd interview. 
 
 
 
This sales leader received 347 resumes for 3 open roles. 
 
They did screening calls with 36 candidates. 
 
Only 3 AEs stood out. 
 
 
Sometimes we overthink. And when we're under stress from needing to find a new job, we can let our best practices slip. 
 
The stand-out sellers treat the interview process like a sales cycle. 
 
When we remember that, and it's not hard to stand out. 
 
 
If you'd like more specific ideas on how to stand out, you might like the $0 "Stand Out" resource I've created. Details here: https://lnkd.in/efDWNsds

Most sellers go quiet between meetings. But that silence is why our deal is stalling. Here's what's really happening:

We think the buyer needs “time to think.”
 What they really need is help deciding.

So *instead* of going quiet, we need to "sell between the meetings."


Here’s are 3 ways to do it:

→ Send info they’d pay to know
 Don’t send generic decks or links.
 Send an insight they’d share with their boss.

→ Match the info we send to where they are in the deal
 New to the problem? Give them clarity.
 Already sold? Give them proof.

→ Always earn the next meeting
 Each touch should pull them forward.
 Not just “checking in” or “bumping this up.”


If our buyer is stalling…
 it’s not always a sign of no interest.
 It’s often a sign they don’t know how to move forward.

Our job is to show them how.


📸: Zora "going quiet between meetings"

Want to make sure your pipeline stays full of deals that go absolutely nowhere? Follow these steps.

1/ Target prospects who've been in the same role for 17+ years. They clearly love disrupting the status quo.

2/ Chase anyone who asks for "more information" after your disco or demo call, but never specifies what. They're def buyers... they want to know more about everything.

3/ To develop Champions, focus on prospects whose only listed LinkedIn achievements are "responsible for" or "oversees." Not "launched" or "drove" or "built." That action-oriented language is overrated.

4/ Extra credit: Multi-thread with anyone whose LinkedIn profile is full of important buzzwords. "Synergistic thought leader driving innovative solutions" ... excellent...

5/ Double Bonus points if they want to "circle back next quarter." Every quarter. 


What did I miss? What would you add?

Kayla closed a $600K ACV deal and secured her President's Club beach chair using this approach. "L-E-A-D".... here's how you can use it.

Premise: If our deals keep slipping, stalling, or ghosting, we're not fighting a closing problem.

We're fighting scattered selling. And scattered selling is a killer.


Here's what helps us overcome scattered selling & move deals forward:

L - Lead the sale
Our buyer is juggling 5 stakeholders, comparing 3 vendors, and terrified of making the wrong decision. If we're waiting for them to tell you what's next, we've already lost.


E - Excavate pain
"What are your pain points?" That's not discovery. Try this instead: "What did you get hired to change?" or "This has probably been a problem for a while. What's making it urgent NOW?"

One question that works almost every time: "Could you walk me through the ripple effects this is having on the business?"


A - Always reduce friction
There are 3 buyer modes: Education (not buying soon), Urgent (needed it yesterday), and Planning (interested but not immediate). Read the room wrong and we're dead. So we ask about *matching* their urgency.

Then teach them HOW to buy: "Typically when companies evaluate this, they involve leaders from Legal, Finance, and HR. Does it make sense to loop them in now?"


D - De-risk to close
Most deals don't die because buyers don't like you. They die because buyers are paralyzed by risk. Your job? Make saying yes feel safer than saying no.


Just dropped a new video breaking down my LEAD framework - the exact system I used to close 6 and 7-figure deals. And helped Kayla earn her President's Club spot by September...

The full video covers the tactical scripts, second-level pain questions, and exactly how to multi-thread without going around your champion.

Stop hoping. Start leading. Watch here: https://bit.ly/47ulyhp


PS-
What's the best advice you've ever gotten on deal momentum?

Most reps say they want to hit 200% of quota. Teddy Frank actually did it.
He set a big goal:  225% of quota. In his first full quarter. And then he hit it.

Closed the biggest deal ever won by a new rep at his company (‼️)
 
Here’s what made the difference:
  - He *asked for feedback.*
  - And then he *actually executed.*

When he was overly focused on closing?
Worked on pipeline.

When his outreach needed tightening?
Built repeatable systems.

No fluff.
 No theory.

Just simple, usable tools:
 → POV Builder
 → Discovery gap analysis
 → Business case templates
 → A negotiation framework that kept margin intact


Teddy’s results didn’t happen by accident.
 He did the work to see his *****blind spots*****
 And he fixed them - fast.


The reps who do that?
 They get to the top of the leaderboard.
 And they stay there.

If you've got some big goals next quarter,
 Blind spots + Building Systems = Where to focus.
🤓

Most salespeople think enterprise buyers ghost us because they're not interested. Wrong. They ghost us because they don't feel understood.

I spent years getting hit with silence, stalled deals, and “we need to sync internally”.

Then I learned something that flipped it for me: Big deals are emotional decisions.

And........ there are 6 emotions that drive every buying decision.
 
When we learn to spot which one our buyer is feeling, the entire conversation changes.

They open up.

They actually engage.

Deals stop dragging.


In my new video I break down:
-->The 6 emotions behind enterprise buying
-->How to read which one your buyer is acting from
-->Questions that make buyers talk instead of hide
-->Why old sales training creates resistance
-->How to make buyers feel seen and safe enough to buy


If you sell to high level buyers, this will change the way you approach every call.

Check the video. This is the stuff I wish I knew years ago. https://bit.ly/49Znxvz

"This was all my idea... so I'm on the hook! 😧" That's literally what my Champion texted me while we waited for the contract to get signed.

And it hit me. While it feels risky to be a seller, it’s FAR more risky to be a Buyer.

Buyers use their social capital to start the evaluation. They convince their team to take the meeting. They navigate procurement and legal and security.

And when Buyers are off doing that work, this is “the silent stretch.” They’re not meeting with sellers.

They’re discussing internally. And it’s this space between meetings where deals live or die.

But most sellers disappear in this stretch.

We think our job as sellers is to show up prepared for calls, ask good Discovery questions, present pricing and handle objections. But Buyers make the most important decisions about us in the moments we're not even there.

They're wondering:
"Does this vendor actually get what we're trying to do?"
Does this product really work for companies like ours?"
"Will they be there when things get hard?"

Here are 3 ways I've learned to show Buyers they matter - especially in those silent stretches:

1/ Send signals that you're listening. 
After a call where someone mentioned a concern, send a 30-second video addressing just that concern. 

2/ Make their job easier before they ask.
 Champions are trying to sell internally for us. Help them ‘connect the dots’ by enabling them with specific resources for specific stakeholders.

3/ Stay present without being in the room.
This is where Consensus  is a game-changer. Every stakeholder can interact with a personalized demo on their own time - and sellers can see what questions they're asking, what features they're focused on, what concerns are coming up.


If those 3 resonate and you want even more ideas on HOW to actually show up with empathy in the sales cycle, join me and Kyle Asay on Tuesday, December 9th | 8am PST | 11am EST | 4pm GMT for a webinar on AI + Human Empathy.

So when we do connect with our Buyers, we’re showing up with empathy and insight. Not just "checking in."

Register here: https://lnkd.in/eVAYvXR2

#ConsensusPartner

Deal reviews need to die. 

Every week, it’s the same meeting. Reps recite updates. Managers nod. Everyone leaves doing exactly what they were doing before.

Sound familiar?


That’s why on November 20th, I'm joining Allego for a webinar that flips this script completely.

Because coaching from sales leadership doesn't fail from lack of caring.
It fails because it's inconsistent, ad hoc, and focused on the WHAT instead of the HOW.


Sellers, think about your last deal review:
→ Manager: "We need to multi-thread this deal." (Rep: "OK but HOW?")
→ Manager: "Build better business cases" (Rep: "Cool. Show me what that looks like?")
→ Manager: "We need deeper Discovery here." (Rep: "Great. What are some questions I should ask?")


We nod but don't know what’s next.
We leave with agreement but no clarity.
Everyone agrees on the problem but no one gets much closer to the solution.🫠 


Hence, the webinar…. Here's what we're covering:

✓ Why your best coaching stays trapped in the sales leader’s head (and how to get it out)
✓ The frameworks that actually change rep behavior 
✓ How AI captures what works - without adding meetings
✓ Real examples of "what good sounds like" that reps can use 


This isn't about AI replacing sales coaching.
It's about making every leader’s wisdom scalable.

So the top performer's discovery framework becomes everyone's.
The best negotiator's talk tracks get shared across regions.
The star closer's techniques don't retire when they do.


Join us on Nov 20, 2025 11:00 am CST

We're keeping it real - no BS, no buzzwords, no fluff.
Just practical ways to turn tribal knowledge into team performance.

Register here: https://lnkd.in/eYNAtvvU


Who else is tired of coaching that sounds smart but never sticks? 🙄

Brand partnership • 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

Things people have laughed at me for spending money on...

 - My own data sources for prospecting
 - Email grading and sequencing tools
 - Public speaking & sales coaching
- Copywriting courses
- LinkedIn courses

My ROI on what I've spent? 
Conservatively...
41.93x

So if you're thinking about doing something that others around you don't quite understand, here's my take - 

Does it ever feel good to have folks snicker and roll their eyes over what we're doing? 

Never. 

And.

When we're willing to do what few others are doing, we get results that few others are getting.

Go for it. 

If you're buying gifts for others today, it can be a good time to reflect on what "gifts" (investments) you want to give your future self this year...


“Twenty years from now you will be more disappointed by the things you didn't do than by the ones you did. 

So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. 

Explore. Dream. Discover.”
-Mark Twain

95%. That’s how much time our buyers spend AWAY from us in any deal cycle (Gartner). Said a different way… the amount of time a buyer spends WITH any one sales rep during the entire sales cycle for B2B is 5%.

But sales leaders scrutinize that 5% like it's the whole job.

They'll dissect your discovery calls. Review your demos. Grade your talk time ratio. Tell you to ask better questions or handle objections differently.

f-i-v-e   p-e-r-c-e-n-t....

Meanwhile, they say almost nothing about the 95% of the time when you're not in the room.

Like when you’re:

→ Deciding which accounts deserve your time and which are just noise

→ Researching executives to figure out how they think and what they care about

→ Mapping org charts to find your champion

→ Sequencing follow-ups that keep momentum without being annoying

→ Managing your pipeline in Salesforce, your tasks in Outreach, your notes in Google Docs, and your reminders on sticky notes.


This is why, when I coach enterprise AEs, we focus on the 95% where deals are actually won or lost.

→ Where you decide if an account is worth pursuing.

→ Where you map the buying committee before the first call.

→ Where you set up systems so you're not drowning in tasks.

→ Where you build the point of view that makes executives want to meet with you in the first place.

AKA: The critical activities they rarely get help with.


What's one thing you wish you had more help with outside of live calls?

The VP ended our interview by saying "We're not hiring anyone in Texas anytime soon." Translation: Thanks, but no thanks. Most people would have just sent a polite thank-you email and moved on.

I did something different.


The Setup:
During the interview, he mentioned a big recruiting meeting coming up in a few weeks. They were scaling at warp speed, BUT he made it clear he didn't see Texas as a priority for hiring.

The VP was focused on the Fortune 500, so he wanted to hire another ENT rep in NYC. (They already had 4.)


My Follow-Up:
As soon as our call ended, I found data showing Dallas ranked #2 behind NYC as the headquarters for Fortune 500 companies. (In a Fortune article, no less.) Yet, the VP had only 1 rep in Texas.

Within 15 minutes of hanging up, I sent him a screenshot with this note:
"Couldn't resist sending this from Fortune, showing Dallas as #2 behind NYC. Seemed like it could be an important data point for your recruiting meeting in a few weeks. More is more on data, no? :)"


The Result:
VP called me back within 5 minutes.
I talked with the recruiter the very next week.
I was the next AE they hired - when they didn't even have an open role in Texas.


Why This Worked:
It didn't just show gratitude - it helped him see a blind spot.
^Just like I'd need to do with prospects who "weren't looking to buy right now."
^^I showed him (in real-time) how I could add value and shift perspective.


The Framework:
--> Listen for upcoming meetings, projects, or priorities during the interview
--> Find ONE relevant insight that challenges their current thinking or adds value
--> Send it fast: screenshot + 2-3 sentence note connecting the dots. Keep it brief and helpful (not salesy)


Bottom Line:
Your interview follow-up isn't just a thank-you note.* It's your first chance to show how you actually work.

Most candidates tell hiring managers what they can do.

Show them instead.


PS-
What's worked for you in interview follow-ups? Share your stories as encouragement (and to spark fresh ideas) for our friends who are looking for new roles!


*PPS-
You should ALWAYS send a thank you note! To everyone you talk to... recruiters, team members, cross functional managers. It is *shocking* how often just that can make you stand out. 🫶

Listen to what happened when a top 1% Enterprise seller used a 1 sentence strategy & won over a Fortune 500 CEO.

Here's how it went down, and how you can do it too.

​
In Q3, one of the Enterprise reps I coach faced a unique dilemma.

​
She had worked hard all year to get a deal going with Lululemon, a $39.2B member of the Fortune 500.

She'd been onsite, worked with ~60 people to multi-thread & come with a Point of View.

She knew her solution was aligned with a C-Level Priority. Problem was, her solution was a small piece of the puzzle and she needed a way to help the CEO understand its importance.

​
A group of champions let the rep know they were presenting to the CEO in a Q3 leadership meeting. 

The AE had to help these champions to show HOW critical her solution was - with a very succinct explanation.
​
​We decided we needed an analogy. 
​

To create the perfect analogy, we went to work researching the CEO. On his public Instagram page, we found our answer.

His Insta was plastered with photos of him & the Lulu team, competing together in triathlons. He'd given multiple interviews on what triathlons meant to his personal and professional life.
​

So we came up with this analogy:

--> "Using the current solution for this initiative would be like using a beach cruiser for the bike portion of a triathlon."

​
If you're unfamiliar with a beach cruiser, it's a bike invented in the 1960's. With the basket in front. Not exactly triathlon material.

Which was exactly why it made the perfect analogy.

​
--> ​"Using the current solution for this initiative would be like using a beach cruiser for the bike portion of a triathlon."
​
​​
The analogy communicated 3 Crucial Realities to the CEO - using language from HIS world:

Their current solution

1/ was OUTDATED
2/ was THE WRONG TOOL for the job
3/ COULD NOT accomplish their objectives 

All without a word about features & functions… which the CEO didn't need to hear about and would have forgotten instantly.
​

​The analogy sealed the deal. The CEO got the picture, and this rep just got a 6-figure Closed Won.

Would that analogy been enough all by itself?

Of course not.

​
This Enterprise rep is a absolute pro, and she'd done all the groundwork.

The on-sites, the multi-threading, the Point of View and Business case.

She had all the right elements. The analogy was the catalyst.

​​
You've got some deals right now where you've laid all the groundwork.

What can you use as your catalyst?

"AI is going to replace salespeople!" But also: "AI writes terrible emails that prospects can spot a mile away!" And: "You NEED to use AI in your sales process NOW!" But also: "AI is ruining authentic buyer relationships!"

Anybody else getting whiplash from the contradictory AI advice flying around LinkedIn?

Meanwhile, back in reality...

Here's what I'm actually seeing with my coaching clients:

Sellers AND sales leaders are getting pressured by execs to "do AI" - but with zero direction on where to start or what problems they're actually trying to solve.

So leaders are buying AI tools. Lots of them.

Without checking if the data is clean enough to even support them.

(Spoiler alert: It usually isn't.)

Here's the thing nobody's saying out loud:
According to MIT research, 95% of AI initiatives fail to deliver ROI.

Not because AI is bad. But because companies are skipping the boring, foundational work - like clean data, integrated systems, and clear processes - and jumping straight to the shiny AI tools.

It's like trying to build a penthouse before you've poured the foundation.🤦🏻‍♀️


If you're getting pressured to "do AI," at least start by knowing where you actually stand.

ZoomInfo just launched an AI Readiness Assessment (built on that MIT research) that benchmarks where your GTM foundation actually is - and what you need to fix before you buy another AI tool.

Takes 2 minutes. Tells you if you're AI Foundation Building, Developing AI Readiness, AI Ready, or an AI Leader.

Plus you get a custom roadmap for what to do next based on your score.

If execs are going to keep pressuring us to "do AI," we might as well figure out if we're set up for success first.

You can take the self-assessment here: https://lnkd.in/efj-tF5A

It’s Thanksgiving. The turkey’s in the oven. My mom’s juggling fourteen sides at once. The kitchen feels like it’s one degree away from absolute chaos.

And what does my dad do? He cranks up the stereo and plays “Pressure” by Billy Joel. 

Followed immediately by “Under Pressure” by Queen and David Bowie.

He’s done this for years (which my mom does NOT find funny). 

Seriously, if you’ve never tried making mashed potatoes while Freddy Mercury is yelling, PRESSURE! at you… 0/10, do not recommend.

Godspeed to everyone in, near or around the kitchen today.

Pro tip: Play some calm music FFS. The "Instrumental Study" playlist on Spotify = gold.



📸: my sweet parents, on a day that is .... not Thanksgiving

Here's why Buyers always say our price is "too high" - whether it's $10,000 or $1,000,000. And 3 ways to fix it.

Problem: Buyers focus on the price of ACTION (our proposals make that cost crystal clear).

But the cost of inaction? That's invisible.


Here's what I've learned after 13 + years in sales:

Even smart buyers genuinely don't know what delay costs them.

They see our $378K proposal. They don't see the $192K in lost productivity bleeding out EVERY quarter while they "evaluate options."


That's why the best sellers don't just uncover problems.

They quantify what those problems cost every day they go unsolved.


I've developed a framework that helps prospects see the full picture - without creating fake urgency or being pushy.

It's based on simple human psychology: people will always find reasons to wait. Our job isn't to overcome every objection.

It's to help Buyers understand that waiting has a price tag, too.


I’m going live this Wednesday 11/19 to show sellers how to quantify the Cost of Inaction, so the buyer feels what’s at stake if they don’t move now. 

This training is normally reserved for my Enterprise Sales Accelerator members, but this week I’m opening the session up for free to anyone who gets my newsletter.

You can join the newsletter list right in my bio, or at krystenconner dot com

Hope to see you there!


PS-
What's the biggest "cost of waiting" you've helped prospects understand when they were delaying a decision?  (And what was their reaction ?!?)


PPS - 
Flashback to when Leslie Venetz and I first joined forces in person. Best NYC trip!!

You open your laptop at 5am.
 Just to “get ahead.”

By 5pm?
 You’re still behind.

No time for prospecting.
 Also - no prep for your calls.
 And the inbox? Out of control.

If you’ve ever thought:
 “I feel like I’m working all day… but not moving the needle”
  and your pipeline is so small it scares you to look at it...you’re not alone.


Here’s what I see happen to so many Enterprise reps:
→ They let their email drive the day
 Instead of choosing what matters most.

→ They underestimate how long things take
 So nothing gets done well.

→ They try to multitask
 And end up doing everything halfway.


Here's some good news:

You don’t need a perfect plan.
 You do need to start with what you can control.

Pick the one task that builds pipeline.
 Put it on the calendar.
 Start with that.

One day at a time.
 One task at a time.
 Keep. Moving. Forward.  


📸: photo with one of the MOST balanced and most successful strat sellers I know 🌎 Jacquelyn Nicholson

The first video I ever posted about Discovery got 23.5M views. So apparently it's not just me that struggles with it. (Because you know what sellers  *DON'T*  get in onboarding or enablement sessions? A simple structure for discovery calls that build urgency. But I digress....)

So here are the 7 Discovery questions I swear by + how to use them: https://bit.ly/47Y0Pmn

PS - 
It's the season of giving, so pls share the best Discovery questions you've ever heard or used.
Even after 13 years in sales, and 7 years as an Enterprise AE, I still "collect" them...

AI is not coming for your job anytime soon:  Exhibit A 👇 

Witness this atrocious visual....mind you that I fed it mounds of my own knowledge & data (correctly spelled, btw)

I'm not mad... just disappointed...


*Friday fun: Which mistakes can you spot? (hint: there are so, so many)

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