SVP, Sales @LaunchDarkly │ Founder, Sales Introverts
Chicago
Joined March 2022
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Having my picture put up on the NASDAQ billboard in Times Square is definitely a career highlight - grateful to be recognized as a GTM10 Award Winner.
A huge thank you to the GTM10 Awards team (Cello and Lightspeed Venture Partners) for this recognition, and to the Sales jury - Mark Roberge (Former CRO at Hubspot), Matt Rosenberg (CRO at Grammarly), Javier Molina (CRO at Docker) and Gaetan Gachet (Founding CSO at Algolia) - for selecting me.
Back to my normal sales tactics posts tomorrow, but wanted to share an exciting professional milestone!
Kyle Asay retweeted
Getting prospect’s attention has gotten so hard we’ve got people thinking about knocking on doors.
I only know one approach that works today across all of our geos and segments and it revolves around “gold nuggets.”
Here’s the 3 step approach our best reps take for breaking through the noise in pipeline generation:
Getting prospect’s attention has gotten so hard we’ve got people thinking about knocking on doors.
I only know one approach that works today across all of our geos and segments and it revolves around “gold nuggets.”
Here’s the 3 step approach our best reps take for breaking through the noise in pipeline generation:
Nothing about this process is easy, but the reps that do it well are having success with outbound.
To help our team stay organized, I built a PG Plan template that we use every week.
You can copy it here (no cost): salesintroverts.com/pipeline…
Kyle Asay retweeted
Can’t imagine a worse signal to send your prospect then “I’ll give you a discount if you don’t compare us to the competition”
Instead:
1) encourage comparison
2) determine most important outcomes
3) tie your differentiators to the outcomes they care about most
4) get buy-in that those differentiators are required for success
This is your brain on bad negotiation coaching from a Harvey sales leader who’s about to miss their quarter.
The point of price negotiation is to offer trade-offs and optionality, so you can uncover the buyer’s real motivation to close and build long term trust along the way.
The approach here kills any chance of that, which is why it’s getting blasted on X.
1. One price for a yes/no by the end of the trial = we’ll pull all effort and resources the moment you sign, because we want to go run the same shitty play on someone else. WE ARE A TRANSACTIONAL COMPANY THAT DOESN’T CARE.
2. Another price if you don’t trial competitors = we want you uninformed, with a weak internal justification for choosing us, so you get fired when the project turns into a massive cost sink.
3. Another price if you decide after the trial = we like to confuse things even further and have never heard of sequential pricing, or of the idea that the buyer’s emotional journey should end with “this was a fair deal that addresses our main goals”, not “my decision-maker is now deeply confused by both me and Harvey”.
Can’t imagine a worse signal to send your prospect then “I’ll give you a discount if you don’t compare us to the competition”
Instead:
1) encourage comparison
2) determine most important outcomes
3) tie your differentiators to the outcomes they care about most
4) get buy-in that those differentiators are required for success
This is your brain on bad negotiation coaching from a Harvey sales leader who’s about to miss their quarter.
The point of price negotiation is to offer trade-offs and optionality, so you can uncover the buyer’s real motivation to close and build long term trust along the way.
The approach here kills any chance of that, which is why it’s getting blasted on X.
1. One price for a yes/no by the end of the trial = we’ll pull all effort and resources the moment you sign, because we want to go run the same shitty play on someone else. WE ARE A TRANSACTIONAL COMPANY THAT DOESN’T CARE.
2. Another price if you don’t trial competitors = we want you uninformed, with a weak internal justification for choosing us, so you get fired when the project turns into a massive cost sink.
3. Another price if you decide after the trial = we like to confuse things even further and have never heard of sequential pricing, or of the idea that the buyer’s emotional journey should end with “this was a fair deal that addresses our main goals”, not “my decision-maker is now deeply confused by both me and Harvey”.
Kyle Asay retweeted
I’ve seen thousands of deals won, and thousands more lost. At this point in my career, I’ve seen deals lost for just about every reason you could possibly imagine.
So I can recognize “trouble” immediately.
I refuse to forecast a deal if any one of these 3 things are true:
3) No “next best option”
Execs rarely put all eggs in one basket (especially with the price of eggs today!) No alternative options to your product most likely means they haven’t committed to solve the problem you address.
Here’s a question you can ask to see how actively they are considering keeping status quo (love this one from Nate Nasralla):
“Who would be happy/relieved if this project was cancelled altogether?”
“You are the [target title] at [target account], and you want to purchase [name of your product] to improve your [use case]. Your CFO wants to be sure it provides business value. Build a business case for [your product], highlighting how it will make the customer money, save costs, and reduce risk.”
That’s a (very) light example of how I use AI to scale best practices across my teams.
I took my approach for:
•PG Planning
•Discovery Prep
•Discovery Scoring
•Business Case builds
•Deal Review/Coaching
And built each into an “AI skill” my team runs to get instant application of my frameworks.
I made them publicly available several weeks ago. Hundreds of sellers have taken advantage, and the feedback has been incredible:
“I credit Kyle’s skill pack as one of the reasons I sit at 113% with over a week left in the quarter”
“I’m 2x more credible walking into discovery calls”
“They’ve changed the way I show up. I feel like I’m getting better every call because of it.”
They are available to all sellers here: shop.salesintroverts.com/pro…
If you are lucky, they’ll go to your website or ask an LLM.
If you aren’t lucky, they’ll just go to your competitor.
Effective modern sales process removes the “give/get” friction and supports both buyer and seller getting the information they need quickly.
Good news for companies and reps that evolve - you can move faster.
Bad news for companies and reps that obsess over “keeping control of the sales process.”
I think sellers should worry a little bit less about “how I do keep control” and a little more about “how do I get the buyer what they need to make a great decision” and let the sales “process” build off that focus.
There are plenty of ways to deploy “give/get” and get the information you need as a seller to run a great sales process without frustrating your buyer.
Because frustrated buyers are no longer sticking around to engage in a sales process they find irritating.