👩🏻‍🏫 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

Jordan Benjamin 🧘

Principal 1 Agency Partner Sales Consultant

I Help Sellers Crush Quota Without Burnout | ex-HubSpot | 🎙 Peak Performance Selling Podcast

𝗪𝗮𝗻𝘁 𝘁𝗼 𝗰𝗼𝗻𝘁𝗶𝗻𝘂𝗲 𝗰𝗿𝘂𝘀𝗵𝗶𝗻𝗴 𝘆𝗼𝘂𝗿 𝗾𝘂𝗼𝘁𝗮 𝘄𝗵𝗶𝗹𝗲 𝗰𝗿𝗲𝗮𝘁𝗶𝗻𝗴 𝘁𝗵𝗲 𝗹𝗶𝗳𝗲 𝗼𝗳 𝘆𝗼𝘂𝗿 𝗱𝗿𝗲𝗮𝗺𝘀?
𝗠𝗮𝗻𝘆 𝗽𝗲𝗼𝗽𝗹𝗲 𝘁𝗵𝗶𝗻𝗸 𝗶𝘁'𝘀 𝗼𝗻𝗲 𝗢𝗥 𝘁𝗵𝗲 𝗼𝘁𝗵𝗲𝗿. 𝗜𝘁 𝘀𝗵𝗼𝘂𝗹𝗱 𝗯𝗲 𝘆𝗲𝘀, 𝗔𝗡𝗗!

🟢 Fact #1. Sales should be one of the most rewarding professions on the planet, but
🔴 Fact #2. According to most recent research 𝟕𝟎% 𝐨𝐟 𝐬𝐞𝐥𝐥𝐞𝐫𝐬 𝐫𝐞𝐩𝐨𝐫𝐭 𝐭𝐡𝐞𝐢𝐫 𝐦𝐞𝐧𝐭𝐚𝐥 𝐡𝐞𝐚𝐥𝐭𝐡 𝐚𝐬 𝐩𝐨𝐨𝐫 𝐨𝐫 𝐟𝐚𝐢𝐫

*𝗪𝗵𝘆 𝟳𝟬% 𝗼𝗳 𝘀𝗲𝗹𝗹𝗲𝗿𝘀 𝗮𝗿𝗲 𝘀𝘁𝗿𝘂𝗴𝗴𝗹𝗶𝗻𝗴* 📉
Most sellers are hungry, driven and motivated to make serious 💰 🤑
But, they live in the land of “what have you done for me lately?” 
They know there’s always more to be done AND
They’ll be back to zero again soon
Even top performers get let go

Sustaining success in sales takes 2 key skills: 𝑯𝒖𝒏𝒈𝒆𝒓 and 𝙋𝙨𝙮𝙘𝙝𝙤𝙡𝙤𝙜𝙮 🧠
Most sellers have #1.  
But they haven’t been taught #2, to train their subconscious to work FOR them. 📈
Most sellers I talk to, think their manager will teach them everything they need for success
That’s a lie your managers job is to solve for the company & then themselves
Another band-aid is NOT the answer 
But they don't have a system

James Clear says it best:
“𝗬𝗼𝘂 𝗱𝗼 𝗻𝗼𝘁 𝗿𝗶𝘀𝗲 𝘁𝗼 𝘁𝗵𝗲 𝗹𝗲𝘃𝗲𝗹 𝗼𝗳 𝘆𝗼𝘂𝗿 𝗴𝗼𝗮𝗹𝘀. 𝗬𝗼𝘂 𝗳𝗮𝗹𝗹 𝘁𝗼 𝘁𝗵𝗲 𝗹𝗲𝘃𝗲𝗹 𝗼𝗳 𝘆𝗼𝘂𝗿 𝘀𝘆𝘀𝘁𝗲𝗺𝘀.”


⭐𝐓𝐡𝐞 𝐏𝐞𝐚𝐤 𝐏𝐞𝐫𝐟𝐨𝐫𝐦𝐚𝐧𝐜𝐞 𝐒𝐞𝐥𝐥𝐢𝐧𝐠 𝐒𝐲𝐬𝐭𝐞𝐦⭐
Helps you:
✅ Use modern science + 2,000 year old wisdom to crush your biggest goals 💰🏡 🛫 👨‍👨‍👧‍👦 
✅ Understand the psychology of what makes people take action
✅ Get the most leverage from each hour in the day
✅ Create a system to elevate your career now
✅ Get free from the sales hamster wheel
✅ Feel better & make more $$

*𝗛𝗢𝗪 𝗪𝗘 𝗚𝗘𝗧 𝗥𝗘𝗦𝗨𝗟𝗧𝗦*
Small personalized changes that deliver massive results
This system has been delivered to 1000s of professionals and has been refined over 5 years to get you the most impact in your life. 
In a short time frame, with simple changes you can create the life of your dreams.

*𝐖𝐇𝐎 𝐈𝐒 𝐈𝐓 𝐅𝐎𝐑?*
High achievers. Sellers that are not going to be complacent with a good life. 
Professionals who know they have more to give to the world and make great $$$ too.

𝗪𝗛𝗘𝗡 𝗬𝗢𝗨’𝗥𝗘 𝗥𝗘𝗔𝗗𝗬 𝗛𝗘𝗥𝗘 𝗔𝗥𝗘 ✌️ 𝗪𝗔𝗬𝗦 𝗪𝗘 𝗖𝗔𝗡 𝗛𝗘𝗟𝗣
1️⃣ DM Me directly. I’m happy to connect and hear what you're working towards and if we can help.
2️⃣ Book a free clarity call to learn if it fits for you (15 min)
MyCoreOS.com/meetings/jbenj/clarity-call

Principal Partner Sales Manager

$1.1Mil dollar club
Top 15 Global Sales Rep
Coached Agency Owners & Sales Teams to Drive Triple Digit revenue growth

I used to get really frustrated in sales
Getting angry with my prospects
Questioning if sales was even for me

But then I made a shift that
Helped me level up my sales game
Lead better and consistently hit P-club was simple

Understanding that everyone I interact with
Internally and externally is also
A human just like me.

They have goals, challenges, fears & insecurities
They have families at home and lots to juggle
They have desires, they get flat tires
And some days don't go
According to plan.

Getting deep into understanding
How people operate
Opened a door

But it starts with understanding yourself first. 
That's why I use this 4 part leadership framework. 

1. Know Yourself
Studies show emotional intelligence
Can account for 90% of top performers success

2. Control Yourself
With knowledge comes great power
Once you can take control, you can be your best

3. Know Others
After the first two now it's much easier
To understand others and what drives them

4. Do Something For Others
Now you're set to lead, to transform and
Help others become their best

This is why understanding people is one of
The most important skills you can build
To be your best at work and at home.

Harsh truth:
Most people are too afraid to start with #1 & #2
Because it takes hard work to acknowledge
Your own flaws and weaknesses

But if you want big rewards, if you want to be your best
You've gotta do hard things.

Understanding people drives business forward. 

Which step are you working on now?

P.S. As you finish the year, It's easy to make it all about you. 
See what you can do to HELP the people you're leading & selling to.
Then the positive results will come.

Helping Sellers Crush Quota And Not Burnout | 6X P-club @ HUBS | SKO Speaking To Level Up Your team | Become A Great Leader

Do something kind for someone today. 


Airport was super easy. 🙏 

Headed to Costa Rica with the family for a non-traditional Thanksgiving because turkey sucks and is always dry. 

Fish tacos this year instead. 🐟 🌮 

Anyone else think turkey usually sucks?

No alternative text description for this image

Jealousy isn't about them winning. 
It's about you wanting it
To be easy

You see someone close a massive deal
Build a million-dollar business
Or Land their dream job

And you think
"They got lucky"
"It happened overnight"
"They have something I don't"

But here's what you don't see

The countless cold calls that went to voicemail
The interviews where they got rejected
The years of building in silence

Nobody posts about
The failed product launches
The heartbreak of deals that fell through
The times they wanted to quit
The days they felt like impostors

I've coached hundreds of leaders and sellers
The ones who "made it overnight"
Actually made it over many nights

Of learning from rejection
Of refining their approach
Of getting back up when it felt impossible

Success isn't about avoiding failure
It's about failing forward faster than everyone else

Your breakthrough might be
One more call away
One more failure away
One more pivot away

The world only sees the highlight reel
And it's easy to assume that
It's easy for everyone else
But that isn't true

Because you don't see the head trash
You don't see the negative self-talk
You don't see the uncertainty

But it's helpful to know
You're not alone

And it's about learning
Every step along the way

What's one setback that actually moved you forward?

♻️ Repost to help others level up from failure
➕ Follow Jordan to learn from failure

Most people think burnout comes from working too hard.

But after coaching hundreds of leaders and sellers…

I’ve learned something far more uncomfortable:

Most of life’s battles happen in your own head.

You’re not fighting:
• a lost deal
• a tough quarter
• a demanding boss
• traffic, email, or your calendar

You’re fighting your thoughts about those things.

The real enemy isn’t the problem.
It’s your reaction to it.

That’s why two people can face the same challenge
one breaks, one rises.

Not because one is stronger…
but because one manages their mind.

If you want to change your performance, your relationships, and your fulfillment…

You don’t need a new job, new boss, or new market.

You need a new mental operating system.

Change the way you think,
and you change everything.

A tool I teach to break distorted thinking and burnout loops.

Whenever your mind spirals take a breath then ask:

1. What else could be true?

This breaks the brain’s tendency to assume the worst.

2. What would the best version of me believe right now?

This shifts perspective and reframes your view.

3. Will this matter in 10 minutes, 10 days, or 10 months?

This shrinks problems down to their real size.

These three questions move people from emotional overwhelm → centered clarity.

They make you a better leader, seller, and human.

What's a way you've updated your operating system?

This video changed how I lived my life
Less than 3 minutes to have a happier life
But most people will skip past it
Because they are too worried
About the small things
That feel big now

The human brain is programmed
To live in the short term

Which means you miss
The most important
Strategic rocks

As you head into the holiday season
Remind yourself what really matters

Getting frustrated with family & loved ones
Is really easy to do at this time of year
You never know when it'll be
The last time you see them

You're replaceable at your job
But you're not at home

What's one of your big rocks?

♻️ Repost to help others be happier
➕ Follow Jordan for more tips to live better

Come ski Vail with leaders & sellers
Ride & Revenue is back and better than ever
A special guest is joining us to start this year

He just finished walking all they way
Across the USA to raise support
And build awareness for men’s mental health
Tim Perreira will join us for a fireside chat
To talk about what drove him to go walk
We’ll discuss corporate burnout
What’s causing it and how to navigate it. 

I actually can’t ski yet this year
So for those who don’t want to ski
We’ll have available co-working space 
At Gravity Haus where you can
Work for the day, network, get coffee & more

But there will also be a group of folks to get out and ski.  

We’ll also have the wonderful Jessie Shipman and some of the Pavilion crew coming up to connect, learn and ride! 

Weds Dec 17th in Vail 
Free to attend
DM me to be added to the list 

Who should come make new connections?

I’ll never forget I was 16 when
My dad told me he had cancer again
This time was different 

The first time, his chances weren’t great
Maybe 70/30 he’d be able to beat it
But I was only 9 at the time
So I was sad and scared
But didn’t get it really. 

This time I was angry at the world. 

I was old enough to question 
My beliefs, my values and
Sense of the world I was building
And the guy who ran a non-profit
Who already had cancer once
Didn’t seem like the type of person
I thought deserved or would get it again. 

There was no denying the truth 
And he handled it with grace again
He wasn’t in the “fight it” camp
He was in the “go with the flow”
Take it a day at a time 
Live with gratitude and joy camp. 

I learned a lot from him during those times
And he beat it so the extra ~20 years
We had after were always a gift. 

Because of that and many other reasons
I’m growing a mustache to raise money
For Movember again this year. 

To support men’s health 
Mental & physical 

Which are two causes that impact all of us. 

$5, $20, $100 is all amazing and when we hit my $1,000 goal. 

I’ll match it with $1,000 of my own.

For yourself, for your friends, sons, brothers, dads. Any donation goes a long way. 

https://lnkd.in/gvjPKaXH

This is for the Lurkers. 
You read, enjoy, and never engage..then
Get on a phone call and say:

"I've loved your content for so long"

Just click the dang 👍 button people!
(not mine or for AI slop but other people's) 🫠 

Vote with your actions. 

Take .15 seconds and click the button. 

End of rant. 

Most creators I talk to say this same thing.
People tell them they love their content
But have never seen them engage.

Help a creator out.
Like the things you get value from. 

If you really want to help them out...
Drop a thoughtful comment
Repost w/out thoughts
Send to a friend
Save it

Just me? 🤷‍♂️

Was going to post about neuroscience & gratitude
But the science behind Laughter + Gratitude 
Is wayyyy better. 

Gratitude is the foundation
Of building a great life

But most people get it wrong
They feel they have to be somewhere else
Before they can be grateful and
That's the worst way to do it.

The universe gives you SO much
When you already feel appreciative
For being lucky enough to wake up today
For friends, for family, for health, for wealth

It unlocks a positive cycle that
Brings even more back into your life. 

Not where you want to be right now?
Be grateful for exactly where you. 
Do it for 21+ days in a row
And your life will change

What are you grateful for right now?

Thanks to the wonderful Jill Fratianne 👩‍🎤 for sending this.  
I'm grateful that you think of me when gratitude comes up!

It's easy to say you want greatness
That's no problem at all
Actually being great, is a big challenge

To get to the top in anything you want to do
It'll take you being willing to do what most WON'T do

Here's what the best in the world do:

1. They show up even when they don't feel like it
Motivation comes and goes
Discipline shows up no matter what

2. They focus on the fundamentals
Success isn't usually a magic silver bullet
It's about doing the basics well. 

3. They build systems to make it easy
A system makes it easy to know what's next
It removes the guesswork and decision fatigue

4. They are always looking to get 1% better
Curiosity isn't something you're born with
It comes from a desire and openness to grow daily

5. They drop the ego
Every professional athlete has a team around them
Coaches, nutritionists, trainers to help them be better

Which one would help you improve the most?

If you want to perform better
Life is too short to spend time 
With people who bring you down.

You are the average of 
The 5 people you spend most time with.

Your family
Your partner
Your friends
Your manager
Your co-workers

Be intentional about your community.

Connect with those that:

- Lift you up
- Cheer you on
- Have high standards
- Push you to be your best
- Give you honest feedback to grow
- See more potential in you than you do
- Are top performers in whatever they do

Having boundaries with those that:

- Complain
- Drain your energy
- Squash your dreams
- Belittle your confidence
- Don't see your greatness
- Only think about themselves 
- Never take personal accountability

These people create the future version of you. 
Find ones who make you better. 

Be courageous to let go of those who don't.

✍ Who is someone that always lifts you up? 

Tag them because sharing that feeling is the best way to grow

♻️ Repost to help inspire others
➕ Follow Jordan Benjamin 🧘 for more

He had millions in the bank
Consistently crushed his job
Lived on the beach.  But it still wasn't enough

You think that if you could:
"Just make some more money"
"Find the perfect partner" 
"Have more free time"
"Land a new job"
"Hit your quota"
"Get promoted"

Then you'd finally be happy. 

Unfortunately, he had all of these. 
But there was still something missing.
So he ended his own life. 💔 

That's another reason why I'm growing a mustache
To raise funds for Movember so we can 
Stop losing men for preventable reasons

I'm only $43 away from my goal
And I'll match the $1,000 raised
Maybe even more if we go over. 

https://lnkd.in/g4Nc-dBQ

Anything counts and goes a long way
To help support men's mental health
To support men's physical health

Thanks for your support!

Open article: Jordan Benjamin's Mo Space by movember.com

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5. Doane University
Becoming an Effective Leader
https://lnkd.in/gTRiJyDM

6. University of Michigan
Successful Negotiation: Effective Strategies & Skills
https://lnkd.in/g44Vk5jJ

7. University of Toronto
Leveraging Your Leadership Self: 
Personal Identity & Behavioral Empathy
https://lnkd.in/gZPiXs6i

8. Harvard
Exercising Leadership: Foundation Principles
https://lnkd.in/gDciGf7w

I thought once I got a degree
I learned everything I would need to know.

But it turns out the learning was just getting started
Because now you have access to the best information
In the world to level up and grow
To be your best

Which one excites you the most? 🤓 
Share in the comments

P.S. Select AUDIT COURSE so it is free ✅ 

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