LaunchDarkly

Responsible for global midmarket sales and BDR functions for net new acquisition and customer growth.

VP, Global Growth Sales

MongoDB

Second-line leader responsible for new business sales for the commercial, mid-market, and lower enterprise segments in North America. 

FY25:

- Q1 129% revenue target
- Increased New Logo quantity while increasing quality (6x increase in acquired customers over $1m TAM) 

FY24:
 
- 163% revenue target 
- Increased Employee Engagement from 59% to 84% 
- Rebuilt struggling org (went down to 8 ramped reps) back up to a team of ~40 while simultaneously going from lowest to highest rep productivity globally)
- Accomplished the above with fewer than 2 inbounds per AE per year and only one SDR covering my entire org

RVP, North America Acquisition

Second-line leader responsible for new customer acquisition for the Midwest, Northeast, and Canada regions.

RVP, High Tech Acquisition - Midwest, Northeast, and Canada

Qualtrics

Responsibility increased to oversee all SAAS revenue for all Midwest accounts up to $2 billion in annual revenue as well as all SMB revenue in North America.

Second-line leader working with a phenomenal leadership team that oversees 60+  fantastic Account Executives.

2021 President's Club winner.

Proudest accomplishments of tenure were:

1) Lowest attrition of any sales leader across the company
2) Helping ten individuals achieve their goals of promoting into leadership roles

Regional Vice President of Sales, Corporate Midwest

Building out our new Chicago office. Second line leader responsible for all Customer Experience, Product Experience, and Brand Experience revenue for Midwest accounts up to $1 billion in annual revenue. Qualified for my 4th straight President's Club. All of my eligible direct reports (Sales Directors) also qualified for President’s Club.

Regional Vice President of Sales, Midwest CX

Asked to take on second-line leadership responsibilities to begin building our new Midwest Market Unit for our CX, PX, and BX product lines.

Director, Corporate Sales

I was the #1 CX Sales Manager for FY 2019 (out of 15+). In addition to being the top performing team as measured by revenue over quota, our group also led out in percentage of reps attaining quota as well as employee engagement. President's Club winner.

Senior Manager, Corporate Sales

I was the #1 CX Team Lead for FY 2018 out of 20+ in my cohort. The highlight of this year / role was Q4 when 100% of the reps on my team exceeded quota which gave us momentum into our record breaking 2019. President's Club winner.

Manager, Corporate Sales

- 2017 #1 Account Executive (out of 200+ AEs worldwide)
-  Averaged 157% of quota across five quarters
- President's Club
- I finished the personal quota chapter of my career story at a cumulative 140% quota attainment ($2.15 million in new business bookings on a $1.5 million quota)

Senior Account Executive

Account Executive

Sales Development

Brigham Young University

- Led team that presented findings to director as well as partner level PwC employees
- Gathered and compiled information relating to most efficient practices that laid the groundwork for process changes within the organization

Field Study Intern with PwC - Team Lead

VP at MongoDB | SalesIntroverts.com | Sellers promote faster with my frameworks

I begrudgingly started my career in sales as an SDR at Qualtrics. After realizing there was no way out, I decided I might as well get good at it and qualified for five consecutive President’s Clubs as an AE, front-line leader, and second-line leader. 

After an incredible 8.5 years at Qualtrics, I was recruited to MongoDB, where I ended my tenure leading their North America acquisition sales organization for commercial, midmarket, and lower enterprise segments. 

After nearly two years of rebuilding and scaling that organization I was offered a role I couldn't pass up to run global midmarket sales for LaunchDarkly. 

When I'm not refreshing my forecast and asking for deal updates from my teams at LaunchDarkly, I'm building frameworks to help other sellers replicate (and exceed) my success. 

You can join well over 10,000 sellers learning from those frameworks at SalesIntroverts.com.

The most uncomfortable call of my career (35 seconds of silence felt like 5 minutes) taught me two important lessons about negotiation.

Here’s the story:

I had a great relationship with my main contacts at an account. We had worked together for over a year, and they were planning on significantly expanding their agreement with us.

Because the license was expanding, they looped in a new stakeholder that I had never met.

This individual’s only goal was to get the lowest cost possible.

We got on a call, and the tone was completely different. The new contact went on the offensive and listed their demands.

The requests were unreasonable. Since I was confident in our solution and the value of our partnership, my response was:

“We’ve been working closely with the team for several months to right-size the agreement and to ensure that the value warrants the investment. While I appreciate your goal is to get the lowest price possible, your requests aren’t reasonable, and we cannot consider them.”

Then, I shut up.

There was silence for what felt like forever (the call recording showed it was only about 35 seconds), and the contact finally said, “Ok. We’ll need to discuss internally.”

The call ended, and we received a signed contract for the proposed amount a few days later.

While uncomfortable in the moment, I learned two essential negotiation lessons:

1) Silence is ok

Be confident, communicate clearly and don’t over-explain. Then, shut up.

2) Saying “no” is ok

When you are close to a deal, it’s tempting to remove all friction by accepting all requests thrown your way.

Don’t. Be confident in your value, and say “no” when a request isn’t reasonable.


p.s. For my best sales frameworks visit hitmyquota.com!

Kyle Asay

I’m frequently asked, “What would you say you do here?” and “We’ll need an hour-by-hour breakdown of your… behavior.”

I spent a lot of time answering these questions, so I decided to record my first (and likely last) “Day in the Life” video. 

Finally, I can easily share exactly how I’m spending my time. 

I hope this video is as fun for you to watch as it was for me to record!

Vague next steps don’t win deals. 

Instead of, “Let’s schedule a demo”

Try:

“We’d love to show you how we help drive [priority outcomes] through [required capabilities] - I think you’ll especially like [key differentiator]. What else would you want us to cover?”


Instead of, “Let’s set you up with a trial”

Try: 

“We’ll get you in the platform so you can see [required capability]. It seems we’ll know it’s successful if you experience [goal after state], any other criteria you’d use to determine success?” 


Getting specific next steps means you have to do great discovery before moving on in your sales cycle. 

If you can’t define specific next steps, you’ll leave your prospect in stage one while you move the opportunity to stage two. 

And prospects stuck in stage one while you think the opportunity is stage two is the first step towards closed/lost.

The funniest cold call I’ve heard happened because we had a competitor called “Ask Nicely.”

The SDR cold called a guy, gave his pitch, and then asked how they were measuring customer experience:

Prospect: “Yeah we’ve got a tool in place for that.”

SDR: “Can I ask what it is?”

Prospect: “Ask Nicely.”

SDR: *nervous chuckle* “Can I please ask what tool you are using?”

Prospect:

SDR:

Prospect:

😂😂😂

Me: "AI could never take me job"

The AI, doing my job perfectly:

7 things I wish I could tell myself on my first day of sales:

1) The success of your career isn’t determined in the first few years. Calm down, deep breaths, get good.

2) You’ll hear “Ok, we’ll sign today” many times. Don’t panic when they don’t. “We’ll sign today” is buyer code for “We’ll sign in 3 weeks when you’ve lost your mind from anxiety and have given up hope.”

3) You’ll win deals you should’ve lost and lose deals you should’ve won. Sometimes it just be like that though.

4) The nicer the procurement person is when you first meet them, the more brutal they will be in negotiations. Don’t fall for it - buckle up.

5) “You are such a good sales rep” is not a real compliment unless it comes with a signed agreement. It’s just a nice buyer that wants to let you down easy.

6) Your potential for success is not limited by others having success, so cheer others on.

7) If you are miserable at work don’t “wait it out.” There will always be a reason to stay (a deal closing, stock vesting, etc.) but life is too short to stay in a job you hate. 

What would you add?

Saying, “yep, that makes sense,” is killing your discovery.

Here’s my favorite coaching method to help reps fix:

When reviewing calls, if I hear a rep say, “that makes sense,” I’ll pause the recording and ask, “did that actually make sense to you?”

9 times out of 10 they’ll laugh and say “no.” It was just more comfortable to move on rather than admitting confusion.

Think about how this feels as a buyer:

1) They just walked you through a complicated problem.

2) They know they didn’t explain it clearly because it’s difficult to put into words.

And they get hit with a, “yep - that makes sense!” in response?

How are they going to believe you have a solution for them if they can’t even believe you understand their problem?

Good sellers have no problem asking for clarification.

Great sellers refuse to move on in a conversation until they are on the same page as their buyer.

Next time you are tempted to say, “that makes sense,” try, “I’m not sure I’m following. Can you explain…” and you’ll have a more meaningful conversation.

7 things I wish I knew as a new AE:

1) No such thing as a “must-win” deal

2) Success is measured in years, not quarters

3) Worry more about the buyer process than your sales process

4) You’ll get ghosted no matter how well you sell

5) $50k-$100k isn’t expensive.

6) Comparison is the thief of productivity

7) No one will care more about your career than you

I break these down in-depth in this video.

What stands out to you? 

p.s. I recently finished documenting everything I wish I knew as an SDR/early AE. If you are in the first two years of your sales career, you’ll love this free resource: https://lnkd.in/g9SZm5wr

“Sales math” used to be simple. Just get your conversion rates for:

Cold outreach -> initial meeting

Initial meeting -> opportunity

Opportunity -> closed won

Throw in average deal size, and you could reverse engineer exactly how many cold calls/emails you need to hit quota.

Now, the math is breaking.

Conversion rates (especially at top of funnel) have gotten so low that this “sales math” leads to impossible to reach volume metrics.

Where 200-400 activities used to generate an opportunity, we now see 1,300+.

So sales reps (and sales leaders) that made a living off of “Well, we’ll just have to do more” are left without a viable answer.

Instead, we need to get hyper-focused on conversion rates:

Less, “Make more calls” and more “Improve the quality of our call list.”

Less, “You need more meetings” and more “How are we making the most of each meeting?”

Quantity will always matter - great conversion across a tiny sample size is a losing strategy. 

But volume alone isn’t leading any company to sustainable revenue. 

I asked eleven top-performing AEs to summarize how they are having success in this “new age” of selling. 

You can copy their habits here: https://lnkd.in/gSmDHXwG

You’d be sick if you knew how many of your hard-fought deals ended with a 30-second conversation between your champion and their boss.

“Sounds interesting, but this isn't a priority right now.”

Here are two questions to ask your champion to see if they are ready to sell:

1) How would you summarize the value of our solution for you and your team?

If they don’t have a good answer to this question, they will not try very hard to sell internally.

2) How would you summarize the value of our solution to your company?

If they don’t have a good answer to this question, they won’t be very convincing when they try to sell internally.

Want to learn how to both motivate AND enable your champion? Take 3 minutes to read this: https://lnkd.in/gmJs2hn2

Soft costs (e.g. ‘our solution will save your team five hours a week!’) aren’t nearly as persuasive as you think.

An executive will think:

“I’m paying them to spend their time working on that problem whether it’s there or not.”

For soft costs to be convincing, you need to have validated a better way for those employees to spend their time.

Weak example:

“We can save your engineers five hours a week if they no longer need to worry about building feature flags. That’s $500k a year of savings, which is 2.5x more than our solution costs.”

The executive will think: “Part of my fixed cost (salary) is to pay them to build internal tooling. I pay them the same, even if they aren’t working on that anymore. I still pay that $500k of salary, and now I’m adding $200k more for a new product.”

Better example:

“We learned from your VP of Eng that if your engineering team had an extra five hours per week to focus on [new product], you’d be able to launch one month early. Your VP of Product estimates the revenue impact of the early launch to be $2 million.”

Take your business case from, “we’ll save your team time” to “you’ll accomplish x and generate $$$ with the time saved” and watch your win rate increase.

Here’s my favorite prompt to see if a top-performing AE is ready for a leadership role:

“Walk me through how you’ve had success as an AE.” 

If an AE can share, in detail, how they’ve had success I’m confident they can teach others. 

If they can’t explain how they’ve had success, how will they help others?

This is why I dislike the phrase, “Those that can’t do, teach.” I think a more accurate statement is “Those that can’t teach, can’t lead.” 

Doers are valuable. 

But someone that can do AND teach can scale success. 

And that’s invaluable.

The worst part of sales for me is being ghosted. Absolutely drove me crazy as an AE.

“Why can’t they just give a quick update?”

“It takes a few seconds to say they aren’t interested anymore… just let me know!”

Now, I understand why people ghost AEs.

Responding with bad news opens up a can of worms:

If they take the time to say “no,” most salespeople ask, “Why?” Then, if they explain why, we’ll try to overcome their objections.

Buyers don’t want this back and forth. It just draws out the process of delivering bad news…

and most people don’t like to share bad news. It’s much more comfortable to stay silent than share a negative update.

I’ve since learned how to minimize ghosting: don’t sell like a seller.

It’s easy to ghost a salesperson. It’s harder to ghost a partner.

Understanding buyer psychology has become a massive advantage.

If that’s something you’d like to improve, join nearly 500 sellers winning more deals by mastering buyer psychology here: https://lnkd.in/gX8wYBva

I’ve hired well over 100 account executives. Here are three traits I love to see:

1) Coachability

No candidate ever has a perfect interview. The candidates we hire recognize where they fall short and request feedback so they can get better.

It’s impressive if you learn (and immediately apply what you learn) in the interview process. Tells me you’ll progress rapidly when given ongoing coaching after being hired.


2) Great questions

We have multiple sales leaders on most steps of the interview process. The candidates we hire have thoughtful and relevant questions for each leader based on their role, tenure, and experience.

How you ask questions in an interview tells me a lot about how you’ll ask questions in a discovery.


3) Internal locus of control

Our top candidates show that they find success despite their circumstances, not because of their circumstances.

Sure, they want to be part of a great culture where they are coached and developed. That’s often a big reason why they are interested in joining my org.

But they understand that they are ultimately responsible for the success of their careers.

This level of ownership helps me be comfortable betting on them.

Any traits I’ve missed?


p.s. Great traits are compounded with elite habits. I compiled the habits of eleven top-performing AEs so you can replicate what works today (free resource): https://lnkd.in/gSmDHXwG

I was promoted to AE after only 3 months as a part-time SDR, even though I wasn’t good. 

Here’s how:

I worked for a startup desperate for AEs, so they promoted SDRs as soon as we knew where the bathroom was.

I definitely wasn’t ready to be an AE, and that’s a big part of why I struggled for two years after the promotion.

SDRs much better than I was have taken a lot longer to earn their AE promotion, because they weren’t in the environment I started in.

Just a reminder to not compare promotion timelines to anyone else:

Their circumstances aren’t your circumstances.


p.s. I recently wrote out everything I wish I knew early in my career. If you are in your first two years of sales, you’ll love this free resource: https://lnkd.in/g9SZm5wr

In my first fully ramped quarter, I sat at $0 on the last day of the quarter before I pulled in a whopping $7k deal to finish at ~10% of quota.

I remember sending my manager a Gchat: “Am I going to be put on a PIP?”

After what felt like a long delay, he messaged back that he would talk to me at the end of the day.

I remember anxiously sitting in the conference room. My manager (whom I deeply respect to this day) came in, expressed his confidence in me, and said he wanted to see my contributions the following quarter prior to any formal performance improvement plan being put in place.

I remember my friends waiting for me after hours, and celebrating with me that 1) I didn’t finish at $0, and 2) I wasn’t on a PIP.

Following that quarter, I doubled down on effort: No one had higher prospecting activity than me.

I doubled down on development: I consumed content from Gong’s research, read the Challenger Sale, and built myself trainings to reinforce those learnings.

I doubled down on ownership: Success or failure was up to me, and I was going to have to accept responsibility for either outcome.

Following that quarter, I only missed once more as an AE (finished at 91% in a quarter two years later).

The trainings I built for myself evolved into trainings I shared with my team.

Trainings I shared with my team became standard for our entire sales org.

Then, I took the best of my learnings from five consecutive President’s Clubs and packaged them into Frameworks that have helped over 4,000 sellers sell more and promote faster.

Sales did not come easy to me. No one has ever said I’m a natural salesperson (my parents still can’t believe I’m in sales lol).

Maybe sales hasn’t come easy to you, either, but perhaps you can accelerate past quarters of struggle with my Frameworks.

See if they are a fit for you at hitmyquota.com!

For the love of human psychology please stop sharing case studies.

Instead, tell stories.

Bad example:

“E*Trade increased ad effectiveness by 47% and reduced their research time by 50%.”

Boring.

Better example:

“The E*Trade team used to spend their time digging through data in excel sheets and arguing about what campaigns to run.

Now, they spend their time attending award ceremonies getting recognized for their ad work.

What would your team do with 47% more effective campaigns while cutting research time in half?“

People love stories. Get good at telling stories and watch your win rate rise.

Maybe you’ve already mastered this skill, and your biggest stress is where to invest your commission checks.

If you want to sell more by mastering buyer psychology, join 641 motivated sellers here: https://lnkd.in/gX8wYBva

Things I don’t post about:

- Cold calling tips
- Scaling companies
- Founder-led sales
- Raising VC money
- Getting on Jen Allen-Knuth's good side

I haven’t cold-called (consistently) in a while. And when I do, I’m not great.

I’ve never scaled a company. Being an SDR, AE, and sales leader at a rapidly growing one doesn’t make me an expert.

As a “founder,” all my sales are digital—so more marketing than sales.

I never have and probably never will raise VC money. Turns out Sequoia isn’t a big fan of businesses built on e-books.

And when (if?) I get on Jen’s good side, LinkedIn will be the first to know. 

I do talk a lot about:

- Hiring
- Coaching
- Retaining talent
- Sales frameworks
- Buyer psychology
- Territory management

I do those things every day, and I’m passing on what works. 

If you want the former, I can recommend some excellent practitioners who share best practices.

If you want the latter, you’ll find my best resources at salesintroverts.com

Stop asking your buyer to quantify their pain as a way to identify urgency early in the deal cycle.

It’s salesy and the numbers are all made up.

Instead, ask “how else have you tried to solve this problem?”

If they haven’t been actively trying to solve the problem, you haven’t identified a real pain.***

If they have been trying (and failing) to solve the problem, you are on the right track.

Save quantifying pain for when you are building a business case with your champion.

Use the “how else have you tried to solve this problem?” question to see if it’s worth your time to build a business case.




***Like everything, there are exceptions to the “if they aren’t trying to solve it today it’s not a problem” concept. Sometimes you teach the buyer about an unforeseen future problem or expose a massive problem they aren’t aware of yet. However, this rule will frequently help you qualify if an opportunity is worth pursuing.

Most sellers rely on "soft costs" to show ROI.

These are things like:

"We'll save you X amount of time"

"Our solution is much more user-friendly"

Here is the problem, though:

Companies already pay for the full "time" via employee salaries.

That is a fixed cost that isn't changing.

So, how do we get deeper and build an impactful business case that (actually) generates ROI?

Find out how in under 6 minutes:

Taplio

Kyle Asay's Linkedin Analytics

Kyle Asay

What is Kyle talking about?

Who is engaging with Kyle

Kyle Asay's Best Posts (last 30 days)

Want to drive more opportunities from LinkedIn?

Taplio

.css-1jgreyo{background-image:linear-gradient(284deg, rgba(39,43,72,1) 0%, rgba(33,47,183,1) 100%);color:transparent;-webkit-background-clip:text;background-clip:text;}Kyle Asay's Linkedin Analytics

Kyle Asay

What is Kyle talking about?

Who is engaging with Kyle

Kyle Asay's Best Posts .css-qqfgvy{font-size:var(--chakra-fontSizes-md);}(last 30 days)

Want to drive more opportunities from LinkedIn?

Kyle Asay's Linkedin Analytics

Kyle Asay's Best Posts (last 30 days)