Kyle Asay

LaunchDarkly

Third-line leader responsible for three sales organizations:

- Global commercial and mid-market sales
- North America Enterprise Acquisition 
- Global SDR

First three months:

- Increased outbound pipeline created by 142%
- Increased outbound pipeline won by 67%

First 6 months: 

- Decreased Time to First Sale from 65 to 33 days (49% improvement)
- Increased Ramped Seller Productivity (revenue per rep) by 45%
- Increased revenue for my segments (US/EMEA/APAC) by 40%
- Drove SDR transformation leading to record-breaking Q4
- Increased PG ARR per AE by 114%

Responsibility increased to cover North America Enterprise Acquisition after impact shown in first two quarters.

Awarded “VP of the Year” and President’s Club for FY25 after completely turning around team morale, culture, while significantly increasing revenue per rep and increasing ASP by 2x. 

Q2 FY25: 73% quota (joined halfway through quarter, assessed org and determined priorities)
Q3 FY25: 85% quota (turned over 50% of team, began rebuild)
Q4 FY25: 91% quota (new reps ramped quickly, rebuild continued)
Q1 FY26: 114% quota (fun to see things working) 
Q2 FY26: 129% quota 
Q3 FY26: 109% quota

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

Missed quota for a couple of years (got close a couple of times). 

Suspended for one day without pay (long story).

Learned a ton, worked hard, results started to come and I earned my first AE promotion.

Account Executive

Promoted to AE after three months of being a part-time SDR because the company was growing very fast and they were desperate for headcount. 

Would have been a lot more successful as an early AE had I actually learned to generate pipeline.

Sales Development

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.

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

The best sales content I’ve read in a long time comes from a buyer sharing how they buy. Today, I'm highlighting my favorite parts along with a little bit of my own commentary.

Let's dive into the highlights, and I'll link the full post at the end.

Highlight one:

“Every vendor tells me their product is revolutionary. You know what’s also revolutionary? Getting fired because your “revolutionary” product bricked the payment system during Black Friday. I’ve seen it happen. It wasn’t the vendor who lost their job.”

Key takeaway:

Sellers all sound the same. Every vendor has “innovation.” Every vendor has “industry awards.” Every vendor has “cutting-edge AI.”

But while we are blabbering on about how great we are, our prospect is wondering: “Where is this most likely to go wrong? And, if it goes wrong, how devastating would it be to me and my team?”

Highlight two:

“The vendor who won my biggest contract didn’t have the best product. They had:

• A reference from a CISO I trusted
• An implementation plan that didn’t require overtime from my burned-out team
• A CEO who personally committed to our success
• Proof they’d done this exact deployment 50 times before

Their competitor had better tech and was 30% cheaper. They also had a 12-month implementation timeline and no relevant references.

Easy decision.”

Key takeaway:

This one is scary. Imagine a forecast call where you tell your boss “my champion told me we have better tech and we are 30% cheaper.”

Sounds like an easy win.

Now, you know that your “champion” could be telling their boss: “This other vendor is more expensive and doesn’t have all the functionality. But it’s the safer bet.”

Your easy win quickly becomes a shocking loss.

Highlight three:

“You tell me features. Tell me what fires you put out and whose job you saved.

You show ROI spreadsheets. Show me CISOs who didn’t get fired after deploying your product.

You push for the enterprise deal. Let me pilot first. Let me look like a hero internally before I bet my career.”

Key takeaway:

You already know features don’t sell - you need to sell “value.” But are you selling the value your prospect cares about?

For most buyers "value" is a combination of “the safest bet to work + most likely to make me look good.”

Highlight four:

“Let’s have an honest conversation. If you keep selling products while we’re buying career insurance, we’re all wasting time.”

Key takeaway:

The job market sucks. Many people (including buyers) are in survival mode.

Are you selling an unrealistic dream? Or, are you selling “career insurance?”

If you are selling the dream, you may find yourself losing to the rep selling insurance.

You can read the full post here: https://lnkd.in/gkPTXFeC

VP Global Growth Sales at LaunchDarkly | Founder of salesintroverts.com

“Ok so let me see if I understand your job. There are AEs that do the work. And they have managers to make sure they do the work. 

Then, there are directors - and all they do is make sure the managers make sure the AEs are doing the work?

And your ‘job’ is making sure the directors are making sure the managers are making sure people are working?

And you get paid money to do this?”

Next time you think it’s easy to be a VP of Sales, imagine how hard it is to convince extended family that your job is even necessary. 

Happy Thanksgiving!

“No one worries about their quota when waiting for test results in the ER.”

I was in a skip level 1:1 the other week when I was asked, “How do you manage stress?” I shared two different “perspective shifts” I use to combat the stress I experience in my role:

1) The “Big Picture” Shift

A few years ago, my wife walked into our baby’s nursery and screamed. I ran in to find our daughter experiencing a seizure. In pure panic, we called 911 and held her while we waited for the ambulance.

As we waited for test results in the ER over several hours, there was nothing more important to me than her health. I could not have cared less about my career, income, investments, car, house, or any of the other “physical comforts” that we often focus on.

Fortunately, tests went well and my daughter remains in great health today.

It also exposed how poorly we prioritize mindshare:

In moments of fear of losing what’s most important, it’s easy and obvious to worry less about what’s unimportant in comparison. 

No one worries about their quota when waiting for test results in the ER.

But when what’s most important is “normal,” it’s taken for granted. And we put our stress/focus on less important things.

When I’m experiencing stress related to work, I do my best to re-center:

“As long as my family is safe and healthy, life is good. Everything else is a bonus.”

Rather than fill my mind with “what can I worry about?” I try to fill my mind with “what can I be grateful for?”

My life is so much more than SaaS agreements and quota attainment, and my stress/anxiety dissipates when my perspective shifts accordingly.


2) The “Great Problems to Have” Shift
​
In the SaaS sales world, I have a fairly stressful role. I’m responsible for several segments of sellers across all geographies. I carry a number that is a significant proportion of the entire company’s revenue/bookings. But whenever I start to feel stressed to the point where it impacts my happiness, I do my best to think:

“What a great problem to have.”

Lots of people would love to have the opportunity to deal with these problems. I have an awesome job, making a great living, working with people I love working with.

So shame on me if I let the stress of the role impact my happiness. And shame on me if I don’t recognize the privilege I have facing these “great problems.”

I’m nowhere near perfect at applying these two shifts - I still struggle with stress and anxiety at times. But the better I get at consistently applying them, the happier I am - regardless of the outcomes I’m seeing professionally.

I have no idea the circumstances you are in today as you read this post. I don’t know the state of your health and your family’s health. I don’t know if you are in a job you love or a job you hate (or looking for work). 

But I hope one (or both) of these shifts help you take on the stress of your life with more optimism and peace.

Ten SaaS sales realities I’ve learned the hard way:

1) If you only hear good news, you are losing the deal. All deals have risk. Champions share risk. No risk shared means no champion. No champion means you lose.

2) The longer it takes to close a deal, the longer your buyer has to realize they are ok without your solution. No velocity, no deal. Time really does kill deals. 

3) Solving a problem doesn’t win deals. Solving THE problem does. Every exec has hundreds of fires burning - they only pay money and spend time to stop the fires that threaten to burn the whole thing down. 

4) More people constantly getting added to the evaluation committee isn’t often a good thing - it means nobody wants to take ownership of the decision.

5) Your buyers spend most of their calls with you multi-tasking. If you don’t quickly capture their attention and keep them constantly engaged, your calls are a waste of time.

6) No one believes your ROI projections. If the business case isn’t in your buyer’s language with their numbers, it’s not taken seriously.

7) Buyers are biased against sellers. Any time you sound the same as other sellers, you strengthen that bias. If you want to win, learn to sound different.

8) You can’t create compelling events (end-of-quarter discounts don’t count). The only consistent way to accelerate deals is to make the buyer’s status quo unbearable.

9) A poorly run deal with a strong executive connection beats a well-run deal with no executive connection. If you have a six or seven-figure deal, and you’re not talking to the C-Level, you’re going to get blindsided by the competitor that is.

10) There is nothing more important to cover at the end of the call than selling next steps. Much better to skip agenda items and align on next steps than to finish the agenda and take next steps “offline.”

What "reality" would you add?

We’ve more than 4xed the number of reps hitting quota in my org over the last year. We even had a team last quarter with 100% of reps exceeding quota. 3 key changes helped us move in the right direction: 

1) Effective pipeline generation plans

We went from reps wondering “what PG should I do today?” to an organized and focused plan ensuring we generated quality pipeline every week. 

You can grab my PG Plan template here: https://lnkd.in/g9sH7Vjq

2) First call preparation and execution

We went from superficial “feature-based” discovery to uncovering business priorities we can solve better than our competition. 

You can grab my Discovery Blueprint here: https://lnkd.in/gT7ZMQQz

3) Territory management

We went from working all accounts evenly to spending 80%+ of our time in our “most likely to win” accounts. 

You can grab my Territory Framework here: https://lnkd.in/gV6uEuRs

I’m grateful to my team for the incredible effort they’ve put in to drive improvement. I’m lucky to work with them. 

I do my best to offer coaching/training to support their success, but they are the ones putting in the effort every day to keep our org moving the right direction. 

And it’s incredible to see our momentum  grow each quarter.

Read a post about a guy that was in the office at 10pm on his birthday. “He has two young boys at home. Most people would have been out the door hours ago. Instead, he’s here, merging new code into production.”

I’m not saying this was right or wrong. There’s a time and a season for different types of “sprints.”

The subject of this post probably more than made up for the late night with dedicated time with his two kids, and all parents make difficult trade-offs with work and family. 

We should NEVER shame/criticize someone for working instead of being with family - we don’t have the context to make that judgment. 

But I do think social media glorifies “hustle culture” way more than it should, so I wanted to share another perspective:

The other day, I scrolled through my digital journal. Went back a few years. 

The last few years have been really good for me professionally. Lots of great quarters (that took a lot of late nights). 

Lots of great teams built (that took a lot of travel). 

But none of that made my journal. 

No entries about late nights working on deals. 

No entries about back-to-back-to-back travel. 

Nothing about “celebrating a huge quarter with the team!” 

Instead, the journal is full of:

- Nighttime stories with kids
- Daddy/daughter dances 
- Family campfires 

This is a sensitive topic for a lot of working parents. Please don’t take it the wrong way - there are ALWAYS tradeoffs and sacrifices. Very few people have the economic luxury of being able to spend all possible time with family - we have bills to pay and people to provide for. 

I’ve had the phone calls while traveling where I hear my kid crying, “I want dad come home.”

I’ve had the dinners when I tell my kids I’m traveling next week and they say, “No, again? Why?”

I wish life was just clean and easy and we always knew exactly what to do, when, and could always be there for people that need us. It’s not. 

But I do think we can do a better job of glorifying the journal moments instead of the hustle moments. 

Because the only way the hustle ends up worth it is if it sets us up for many more journal moments.

And the only way the hustle is sustainable is if we can have journal moments along the way.

Jen Allen-Knuth said something brilliant (I know, I was shocked as well) when she mocked poorly planned AI approaches with the phrase: “Our efficiency > their experience!!!”

I’m seeing this a lot right now where companies are 100% trading “efficiency” at the cost of their buyer’s experience. 

Companies are planning how they can:

- Automate prospecting to save THEIR company time

- Cut out human interactions with buyers to save THEIR company money

Without spending nearly enough time/effort asking “how can we make buying better for the buyer?” 

Don’t get me wrong - I’m not anti-scale. 

I’m definitely not anti-AI. 

I just think we need to draw the line. 

RevOps and sales leaders SHOULD obsess with scale/AI/automation:

“How do we leverage systems to quickly get sellers the right leads, in the right accounts, understanding which signals should drive their outreach?” 

AEs SHOULD obsess with scale/AI/automation:

“How do I leverage systems to quickly get account point-of-views, build business cases, build account maps, etc.”

It’s insane what we can do with the above now compared to just a couple of years ago. It’s really exciting. 

But after all that effort to get the right person, at the right time, with the right context in front of sellers PLEASE don’t blow it by scaling the “last mile” where human to human connection is possible. 

Once it’s time to start a human conversation, don’t ask “how do we scale this?”

Instead, ask, “How do we execute plays that can’t be scaled?” 

It might be a handwritten note. It might be a custom gift. Maybe it’s executive to executive outreach. Maybe it’s a video you record yourself. 

There are lots of ways that you can “stand out” from the AI-automation that’s clogging every executive's inbox. 

And not one of those ways can be “scaled.”


p.s. If you want help leveraging AI for the right use cases, I built out an AI prompt guide that will help you identify key accounts, build value props, and draft compelling business cases here: https://lnkd.in/gKpSUNtj

Taking credit for other people’s work is a VP of Sales superpower but I have to be honest:

Even the best sales training in the world does nothing without a TON of individual effort to apply what is taught. 

I have zero “just say this to close deals” scripts. 

I have zero “this play ALWAYS works” tactics. 

But I have built a collection of resources that, if you put in the effort to apply, will lead to you having more success. 

I’ll keep adding sales training that can help you sell more. 

I’ve already added Kyle GPT to give you real time insight on ANY sales related question (feedback has been incredible). 

I’m launching a beta version of a new application shortly to accelerate PG planning and discovery preparation.

But it’s on you to put in the work to apply.

If you are willing to put in the work, all you need is available here: https://lnkd.in/ghXnxaQw

What’s going on at LaunchDarkly? I’ll share a few things:

- Seller productivity more than doubled YoY
- Average deal size up 45% YoY
- Win rates over 40%

We’ve experienced a complete transformation over the last several quarters. 

A few reasons why:

1) Incredible product

Our logo retention is in the high 90% range. Selling a need-to-have product that customers love is the key foundation for GTM.

2) Incredible team

We’ve hired incredible leaders and reps across all segments and geographies. 

And our tenured reps that have stuck with us through the transformation are absolutely crushing their targets. 

We have a great mix of new AEs ramping well with tenured AEs leaning in with mentoring while blowing through revenue targets. 

3) AI Tailwinds

We help organizations de-risk their software releases: 

AI assisted code generation -> more code -> larger risk radius. 

AI applications rely on non-deterministic models. Non-deterministic behavior -> increased risk. 

LaunchDarkly helps engineering teams get the best out of AI without the risk exposure caused by AI. 

And this market is booming. 

We are hiring across nearly all departments to support our growth. Check out our careers page to learn more. 

And if you are an elite acquisition/new business AE, reach out to Saramarie Malone (Shine) . 

Because that part of my org is growing!

I was tasked with completely turning around multiple sales orgs when I joined LaunchDarkly. As we’ve gone from nearly everyone missing quota to blowing out targets the key 3 metrics I measure have stayed the same: 

- This quarter’s revenue 
- This quarter’s AE-sourced pipeline
- Next quarter’s pipeline coverage 

I measure this quarter’s revenue because duh. 

I measure this quarter’s AE-sourced pipeline because it’s fully controllable. Even if a rep is having a bad revenue outcome this quarter, they can excel in this area. 

I measure next quarter’s pipeline coverage because it’s the best indicator for future success AND it’s fully controllable. Even if a rep is having a bad revenue outcome this quarter, they can excel in this area. 

I clearly communicate expectations (for ramped AEs) against these three goals:

0/3 is unacceptable.  

1/3 requires immediate change in behavior.

If you are 2/3, you are on the right track.

If you are 3/3, you are on track for promotion. 

Simple, and based on the results we’ve seen, effective. 

If you want to copy the PG Planning system we use to drive strong results across these three metrics, you can grab it here: https://lnkd.in/g9sH7Vjq

Copy/paste this prompt (or save this post) to bring the ideal point-of-view to your next discovery call:

This prompt works well because it surfaces likely priorities for the team you are talking to AND the company - along with how they go together. 

Team priority = something your potential champion cares about solving 

Company priority = something worth funding 

Here’s the prompt: 


"I am a sales rep at [company]. I have an upcoming conversation with the [prospect title] at [prospect company]. I want to come prepared with a point of view. The point of view should include:

- Company Focus Areas
- Team Focus Areas

The company focus areas and team focus areas should be related.

The team focus areas should support the company focus areas.

Each company focus area should tie back to a team focus area and vice versa.

All focus areas should be based on recent news about the prospect's company.

All focus areas should also be related to the value proposition of my company.

Conduct sufficient research of my company and the prospect's company to ensure the point of view is specific and relevant.

Return three bullet points for each focus area."


I’ve had a lot of success teaching ChatGPT my frameworks for selling when using the tool for research, so I built a resource that allows you to do the same.

A short sequence of prompts to find ideal fit accounts, build a point of view, and generate a mini “business-case.”

You can grab it (no cost) here: https://lnkd.in/gKpSUNtj

One of the least “fair” sales realities is that average sellers in great environments usually earn more than great sellers in average environments. Here are 3 ways to identify a great environment (starting with 2 critical metrics):

1) Gross Retention Rate

Gross retention rate is how well you preserve your existing renewal base. Basic example: If a company has 10 customers spending $10,000 on average, they have a renewal baseline of $100,000. 

If one customer that spends $10,000 doesn’t renew, their gross retention is $90,000, or 90%.

90%+ is good. 95%+ is great. 

2) Net Retention Rate

Net retention measures how much your customer revenue base grows each year. After you take out the lost renewals, and add in the renewals + expansion, is your customer base growing or shrinking?

110% is good. 115%+ is great. 120%+ is best-in-class. 

3) Quality of Sales Org

There are a lot of tools to identify the quality of a sales org (Glassdoor, RepVue), etc.

These are great places to start your research, but I know of sales orgs with great reviews where the team is miserable, and sales orgs where scores are “meh” but people are happy and crushing their comp plans.

So validate what you are seeing with the people that know best: current AEs at the company you are evaluating. Try and talk to at least three, otherwise you may talk to an outlier.

Finding a company with great metrics is a start.

Finding great metrics and an incredible sales org will make your career. 

I put together a list of questions you can ask to make sure you are looking at a great sales org. The questions assess:

- Product strength
- Executive team support
- Sales leadership effectiveness
- Compensation plan quality and upside

You can read it here: https://lnkd.in/ghzKbbbd

I got a LinkedIn DM from someone that said, “I just lost a deal because I multi-threaded to a CEO and went above my champion. He said I betrayed his trust and had a hidden agenda.”

Brutal.

Then he made a great point: Everyone talks about how to multi-thread. No one talks about what not to do.

So here’s my short summary at what not to do in multi-threading:

1) Don’t go over the top of senior execs

2) Don’t surprise your champion

3) Don’t neglect your contacts

I went deeper into this subject to teach you what NOT to do when multi-threading in a previous newsletter. 

Get all the details you need by reading this (2 minute read): https://lnkd.in/gKmHAi8q

AI slop is killing sales, but sales orgs that don’t adopt AI will die. 

Yikes - what a dilemma. 

The “AI in sales” debate is the most interesting and impactful “fork in the road” that I’ve seen in my career. 

It’s an interesting dynamic - sales execs are pressured to evaluate and implement AI tooling, while they ignore the hundreds of messages bombarding their inboxes from the companies implementing AI tooling. 

Companies that over-rotate to AI may find themselves “marked as spam” into oblivion. 

Companies that don’t rotate enough may find themselves sinking into irrelevancy. 

I don’t have all the answers. 

I don’t have a PDF that breaks down “how I bring in millions of revenue without sales reps using AI” that you can comment “SCAM” to get. 

But I have spent a lot of time evaluating AI solutions while also managing highly productive sales orgs, and I have strong opinions around balancing tasks suited for AI with engagements suited for human empathy. 

I’m really excited to go deep into this topic with the brilliant Krysten Conner in Consensus’ upcoming webinar: AI + human empathy in sales

You can join live or get the recording by registering here: https://lnkd.in/gUkR2nhC

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

Consensus

IMO, the perfect discovery nails three points: 

1) The conversation is centered around a problem worth solving 

2) You uncover current state and negative consequences

3) You give your prospect enough confidence you can solve their problem that they agree to a next step

Today, I’ll give you the AI prompt I use to make sure we are ready to find a problem worth solving. 

This is the most important part of discovery, because if you run “great discovery” around a small problem, you end up with MEDDICC filled out but no next steps. 

Good for CRM hygiene. Bad for quota attainment. 

Successful discovery doesn’t start until you’ve found a problem worth investing time and money to solve. 

I recommend this prompt to bring to discovery a “point-of-view” to quickly validate problems worth solving (copy/paste or save the post to keep):

“I am a sales rep at [company]. I have an upcoming conversation with the [prospect title] at [prospect company]. I want to come prepared with a point of view. The point of view should include:

- Company Focus Areas
- Team Focus Areas

The company focus areas and team focus areas should be related. The team focus areas should support the company focus areas. Each company focus area should tie back to a team focus area and vice versa. All focus areas should be based on recent news about the prospect's company. All focus areas should also be related to the value proposition of my company. Conduct sufficient research of my company and the prospect's company to ensure the point of view is specific and relevant. Return three bullet points for each focus area.”


One of my favorite parts of Attention is the ability to score calls with a “custom scorecard” - including weighting for different categories. 

Because “great discovery” is a lot more than being able to fill out MEDDICC, and their level of customization allows revenue orgs to measure what actually converts to revenue. 


*The screenshot attached to my post shows my custom scorecard (including how I’ve weighted the “finding a priority” as 2x more important than other scoring categories - you can’t run successful discovery without it!).

Attention

My #1 priority when joining LaunchDarkly was to improve pipeline generation. Three tactics we used to improve by 142%:

Tip One: “Bucket Your Buyers”

Most companies sell to a few different personas. 

All companies sell to different levels of those personas. 

If your list “scrambles” them altogether, you are putting yourself into constant context switching. 

Instead, keep similar personas grouped together so you can get in the flow with value drivers, customer stories, and use cases. 

 
Tip Two: Dig for Gold 

We don’t make all calls with the intent to set a meeting. Sometimes, we are just looking for a “nugget” we can use to set a meeting with an above-the-line contact. 

When we get “gold nuggets” like project names, executive KPIs, or even just current tooling challenges we use them to nail our calls to “decision makers” where we want to spend more time. 


Tip Three: Problems, Not Product

Our messaging used to be all about us: 

"We are a feature flagging platform that allows developers to separate deploy from release, toggle features on or off..."

Now, we lead with problems we solve:

"I'm reaching out because I noticed your team's focus on AI-driven development to increase velocity. 

A lot of engineering leaders we talk to are sharing the challenging trade-off between speed and risk: more code with less time for testing means more potential for things to go wrong at release.”

What’s more likely:

Your prospects are facing the problems you solve? 

Or

Your prospects are actively shopping for what you do?

Message accordingly, and conversion will increase. 

We drive (and track) these tactics through our “PG Plan” template. 

It’s worked well for us, and it might work for you as well. 

You can copy it from us (at no cost) here: https://lnkd.in/g9sH7Vjq

I botched one of the most “well-prepped” discovery calls of my career. 

The meeting was with the CMO of a large law firm - the ideal target for our new brand tracking solution. Before the call, I did tons of research on his firm, the market, and relevant trends. 

But he shut me down before I had a chance to share my “expertise.” And it was completely my fault. 

He didn’t know I had done my research. He had no idea I was prepared. He assumed I was like most salespeople:

- Didn’t understand him/his role/his priorities
- Would try to push my product
- Wouldn’t listen to him

Everything went wrong with my first (and last) question:

“Can you tell me about your role?” 

Looking back, this question was unnecessary. I knew a lot about his role from my research. But he didn’t know I knew, and my question made it sound like I was clueless.

His response (in a very irritated tone) was:

“Kyle - you asked me for this call. Why don’t you just tell me what you do.” 

Blerg. 

I stumbled over my value prop, trying to make it as specific as possible based on the research I had done. But the CMO had already mentally checked out, because he had already determined that I was “just like all the other salespeople.” 

And most salespeople don’t make good use of an executive’s time. 

That painful lesson completely changed how I ran my discovery calls. I learned that sellers are guilty until proven innocent, and I had to show up strong in the first few minutes of the call to earn a buyer’s attention. 

Since then, I’ve improved my discovery framework. No more irritated buyers, no more wasted opportunities. 

And I’ll teach it to you for free today here: https://lnkd.in/gT7ZMQQz


p.s. completely irrelevant picture is included because it’s hard to beat the fall views on my street. You are welcome it’s not an irrelevant selfie.

“Can I just have a trial” can mean a few things (some good, most bad). Here’s the question you can ask to find out where you stand:

“What are you hoping to test?” 

A couple potential responses:

1) They give clear answers

This is a good sign that they are actually evaluating, not just trying to brush you off.


2) They say “Not sure, just want to play around.”

This means they are either:

- Brushing you off
- Interested, but unsure how to evaluate 

Ideally, you don’t end up in too many deals where your prospect wants to take complete control of the evaluation. 

But my career in sales (and lots of mistakes) has taught me that you need to know how to win even when you find yourself in less than ideal situations.

I recently wrote an article that covers: 

- How to test for sincerity
- How to maintain control of the evaluation
- How to increase the chances of a successful trial
- A trial checklist template you can use to increase your win rates

This article will NOT be relevant to sellers that aren’t in a PLG environment. If your company doesn’t offer trial accounts through your website, no need to read. 

If your company does offer trial accounts, reading and applying this might be the difference between winning and losing your next deal. 

You can read it here: https://lnkd.in/gQHaU7Uv

Bad data nearly cost me my job less than 2 years into my career. 

Well, technically, my poor response to a territory deployment built on bad data nearly cost me my job. But that’s a less fun “hook” to a post. 

Here’s the story:

We were growing fast and we needed to completely redesign territories. The approach of “reps grab whatever accounts they want” wasn’t going to work anymore. 

SalesOps built a solid scoring algorithm. It had core criteria to score accounts:

- Industry
- Revenue
- Employee count

They pulled all of our customer data to see what “great fit” looks like, and could predict potential spend nearly perfectly when the algorithm was applied to current customers. 

The approach/weighting/algorithm was well designed and well tested. 

The next step was to create geographic territories, based on zip codes. They’d take all the accounts in a zip code, score them, and then sum up all the accounts to give the zip code a score. 

The logic was sound: if we know the score of a zip code, we know how much revenue to expect from that area. Then, we just need to give enough zip codes to each rep to make sure the total score is enough to support their quota. 

My territory ended up as  suburban Grand Rapids, Michigan. All the zip codes in the area that weren’t in the metro/city. 

When I dug in, I immediately found a massive issue: I had accounts that were scored high that actually sucked. 

The problem wasn’t the algorithm used to score the data. It wasn’t the zip code based approach. 

The problem was the data powering the model. 

I’d look at accounts that our data said had 750 employees and $300 million revenue. Reality was they had 14 employees and not enough revenue to build a working website. 

Out of my 2,000+ accounts, maybe 20 were actually a good fit for what we sold. 

So I threw a fit and nearly got fired (ended up suspended without pay for a day - bless up merciful sales leaders!) 

But that’s not the point of the story. The point of the story is that the great algorithm and strong strategy failed because the underlying data wasn’t accurate. 

And now, with AI, companies are able to make really bad decisions EVEN FASTER because their fancy AI tooling and strategy is powered with incomplete or inaccurate data. 

ZoomInfo is one of our critical partners to make sure our AI strategy is fueled with accurate data. They’ve built an assessment that will help you see if your GTM Org is ready for AI success. 

I took it and it showed some clear recommendations for where my org can get better. 

You can take it here (takes less than 5 minutes): https://lnkd.in/gJBgftDE

Brand partnership • VP Global Growth Sales at LaunchDarkly | Founder of salesintroverts.com

I love helping others make a lot of money. 

Now, to be fair, this isn’t a purely benevolent desire. 

The more money my team makes, the more I make. 

And as Sales Introverts customers make more money, more people sign-up for Sales Introverts. 

So I’m gonna keep helping as many people as I can to make more money. It’s a classic win/win. 

Notes like this are awesome - sellers aren’t just closing more deals by applying my trainings, they are getting life-changing job opportunities. A 60% OTE increase is crazy! 

I’ve built a collection of resources to help you make more money immediately (the same this seller used to get a 60% raise):

- Kyle GPT (ask my sales brain anything)

- AE Operating System (everything from landing a great job to earning promotions)

- Deep dive video trainings with the same lessons I teach my teams at LaunchDarkly 

Plus tons of other resources (AE Frameworks, Leadership Frameworks, Buyer Psychology, etc.)

People are adding 10s of thousands of dollars to their W2 after investing $29/month. We’re talking 10,000%+ ROI. 

No wonder my business partner keeps “suggesting” we raise the price. 

We will definitely raise the price soon - the amount of content in this offering is already crazy and it grows every month. 

But anyone that signs up during the “launch” will lock-in the entry price as long as they stay enrolled. 

I’ll keep building. 

You can join whenever you are ready: https://lnkd.in/ghXnxaQw


(I blurred out the other trainings mentioned because they are awesome content created by great people. It’s really cool that this Insider found Sales Introverts uniquely valuable, but I don’t see a reason to “compare” to others.)

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