👩🏻‍🏫 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

Productside

Account Executive

Espressive

Waiting on hold for IT is a pain. Particularly when it can take hours to days to get a simple fix. 

Imagine if Alexa or Google Home could hear your request,  and automate the fix 70% of the time.  For the remaining 30% they create the support ticket for you and assign it to IT getting you help faster.

Espressive uses its own LLM and conversational AI platform (Barista) to do just that.

IT can focus on high value activities instead of tickets. Employee's get help instantly. Companies don't have to build complicated AI models and get results day 1.

 It's a win/win/win!

***
- Hit 129% of annual quota in 8 months in 2022 
- Hit 135% of annual quota by end of Q3 2023

Senior Enterprise SDR & ISR

Sales Development Representative

Swag.com

Swag.com helps companies create and distribute quality swag that people actually want to keep. Thousands of companies (including Facebook, Google, Amazon, Microsoft, Harry's, Starbucks, Uber, Spotify, Netflix and Tik Tok) use our swag to drive employee engagement, welcome new hires, attract and thank key clients/referral partners, make their events (virtual or otherwise) more exciting and more.

I was their first outbound sales hire, building the playbook for cold outreach from scratch.

Business Development Executive

Paychex

Paychex, Inc. (NASDAQ: PAYX) is a leading provider of integrated human capital management solutions for payroll, HR, retirement, and insurance services. Paychex has been named among the World’s Most Admired Companies by Fortune magazine, ranked among the best training organizations in the world by Training magazine, and recognized as one of the world’s most ethical companies by the Ethisphere® Institute. More importantly, over a half million businesses place their trust in Paychex every week.

Built around a fusion of data, technology, and service, Paychex FLEX Enterprise represents an unmatched commitment to you and your business.

Because people are at the core of Paychex FLEX Enterprise, we call it truly human, human capital management.

Major Market HCM Consultant

Gartner

Engage large enterprise C-Suite level executives to schedule sales introductions, convert leads, facilitate discussions, support the sales cycle and generate new business 

Partner with Business Development Manager to achieve quota of $750,000

Gather and analyze business intelligence to qualified prospects, companies, and leads 

Maintained high level of performance FY2017 exceeding goal during integration after being acquired by Gartner

Completed CEB’s 2 year Sales and Service Professional Development training program. Promoted from Business Development Associate to Business Development Specialist to Senior Business Development Specialist

Senior Business Development Specialist - Gartner for Sales Leaders

500+ member sales executives use Gartner for Sales Leaders in order to drive growth, improve efficiency, benchmark performance against best-in-class metrics, and achieve critical business objectives through successful talent and functional strategies. Clients have access to the guidance and tools that enable business leaders and managers to overcome common challenges, implement proven best practices and drive the organization’s performance.

Business Development Specialist - Gartner for Sales Leaders

CEB, now Gartner

Business Development Specialist - Communications

Business Development Associate

•	Cold calling to define new prospects and arrange initial meetings
•	Profiled clients and updated Salesforce.com database
•	Developed Excel management dashboard based on SFDC outputs 
•	Initiated and created the 2014-2015 marketing “FedEx Mailer Campaign” 
•	Drove attendance to an ADP ACA Seminar through cold calling and email campaigns

Sales Intern

Marlboro Swim Club

Ensuring smooth execution of daily operations and managing a rotating staff of twenty guards.

Life Guard Supervisor

ATA Marlboro

•Welcomed new students into the dojo and made them feel comfortable.
•Taught age groups 4-60 martial arts.
•Led classes upwards of 10 people.

Assistant Instructor

When I was little my dad used to call me the “Mayor of the Playground”. I would walk up to anybody and say “Hi my name is Sam, want to play?”

Now as a determined professional I still strive to be just as charismatic, but now my goal also includes being a reliable, honest and insightful resource for my clients. I am passionate about helping organizations overcome their challenges, celebrate their success and achieve their vision.   

Feel free to add me for networking opportunities. 


taplio

The Battle

👩🏻‍🏫 Krysten Conner

Sam Ackerman, (MBA Candidate)

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