Isaiah Crossman

Partner @ Repeatability

[Isaiah Crossman @IsaiahCrossman]

Calculating win rate as [won] / ([won] + [lost]) for a given quarter has always struck me as not that useful.

- The results are easily swayed by data hygiene or inconsistent handling of when opps are marked closed lost (like one quarter where lots of opps are marked lost at the end of the prior quarter and start of the following one will have an erroneously high "win rate")

- Sample sizes are often too small to compare reps to each other (or to read into small changes from one Q to the next)

- No good way to account for open opps

If you're SUPER tight and consistent it can be a decent directional indicator over time.

I DO however like win rate by CREATED DATE cohort where all the opps from the group are closed, one way or the other. That's the TRUE win rate for your sale (even if it's a lagging indicator).

[Isaiah Crossman @IsaiahCrossman]

@saas_seller Good teams with all the right context to be able to attract top talent can get like 80% right w experience, good mock calls, etc. But some teams have to take chances on more up-and-comers etc where you're betting on attributes to convert into skills (obv lower hit rate).

[Isaiah Crossman @IsaiahCrossman]

@natolisnuggets Yeah on pure economics that makes sense and is reasonable if that's someone's primary consideration. My point re prospects is about the signal it sends for future potential (but similar if you're selling more and more usage to those same people now too I guess).

[Isaiah Crossman @IsaiahCrossman]

INSANELY important sales lesson:

[Shane Parrish @shaneparrish]

Ryan Serhant explains the art of following up.

There are 3 F's.

1. Follow up
2. Follow through
3. Follow back

"Follow up forever. Until people buy, die, or don't want to work with you."

[Isaiah Crossman @IsaiahCrossman]

If you're losing deals that FEEL like they are a great fit and should buy, it's probably because you failed to get the customer to understand the true total VALUE your product will deliver.

The biggest value is often something their executives really care about (I call this an Exec Team Priority), like:

- New revenue they can't get better some other way
- REAL cost savings
- Security
- A key to a real Named Project at their company
- Time savings that reduce the need to add hires
- You get the idea... big stuff

Again, losing deals that FEEL winnable is very often downstream of failing to get your customer to see your product as delivering one of these outcomes.

[Isaiah Crossman @IsaiahCrossman]

@collin_ruth89 We worked with @TeddyEMoss and it was insanely valuable. Know another company that worked with him and said similar.

[Isaiah Crossman @IsaiahCrossman]

I have Grok @bot check my email every 15 min and draft replies to anything that needs one.

Started by having Claude Opus 5.5 go through my email and write a style guide for my voice. Gave that to my bot.

I didn't edit this email at all. Quick read, hit send.

Other benefit is when I see the red "Draft" in my inbox I know it means it requires a reply.

[Isaiah Crossman @IsaiahCrossman]

@BrianLaManna_ That guy is one of the most iconic linkedin trolls

[Isaiah Crossman @IsaiahCrossman]

@headsetpipeline lol yup

[Isaiah Crossman @IsaiahCrossman]

@TechSalesGuy Yep. As a general rule, in my experience, the number of call recordings a new hire (or SDR > AE promo) listens to in their first few weeks is directly correlated with long term success in the role.

[Isaiah Crossman @IsaiahCrossman]

Virtually every AE has faced some version of:

"unfortunately our CXO wants us to take a few months and see what we can build in Claude before moving forward"

We're hosting a live 45 min workshop on how the best AEs handle this:

- Talk tracks
- Example visuals
- The best overall narrative we know

Next Tuesday at 12pm est

Sign up (free): https://t.co/65WhKivETD

[Isaiah Crossman @IsaiahCrossman]

@pipelineclub100 Yeah I could see it

[Isaiah Crossman @IsaiahCrossman]

Great lesson. Love sales examples from the real world.

Tech sales equivalent is when you're on a first call talking about how you'll solve a specific problem for the customer, just saying "here, I'll show you..." and sharing your screen for 30 seconds.

[Max Palmer @MaxNPalmer]

The retail rep at Buck Mason just pulled a great sales trick on me.

I asked about their Oxford shirts. They didn't have any on display, so he went into the back to grab them.

He came back out to the showroom and told me he's put them in the dressing room ready to try on. He didn't bring them to the showroom for me to see. He knows I'm most likely to buy if I try them on, so he made it as easy as possible for me to do so. "They're already in the dressing room ready for you."

I try them on, love one of them, and buy it.

Reminder to always make it as easy as possible for someone to buy from you.

[Isaiah Crossman @IsaiahCrossman]

@alistairmcleay Caught a $40,000 mistake from our accountants this way.

[Isaiah Crossman @IsaiahCrossman]

If you're in sales and you've been following up on the same email thread 2-3x and you're getting ghosted send your next email on a brand new thread and pretend like absolutely nothing is wrong. Totally run of the mill communication.

Almost never fails (if it's a real deal).

[Isaiah Crossman @IsaiahCrossman]

Cold call openers: the main goal of the “opener” is just to create the most organic possible opportunity for you to give a quick pitch and see if it’s interesting to them.

For example: “Bill, it’s Isaiah calling from Repeatability… how are ya?”

Them: “Gooood… sorry, from where?”

Boom.

Opportunity to say the most compelling two lines I can possibly muster about my product (getting THIS right is the actual hard part).

[Isaiah Crossman @IsaiahCrossman]

@ImAntCalabrese Issue w this approach that I see is that evvvveryone is doing a version of it so it becomes a pattern that customers learn to filter out

[Isaiah Crossman @IsaiahCrossman]

@therealDakBrown Sooooo situational. That's a solid formula for a summary after a call (though I think this formula is pretty much a commodity now due to AI and not that impactful).

In the original message I'm actually talking more about follow-ups AFTER the first message.

[Isaiah Crossman @IsaiahCrossman]

If you’re in sales you need to be careful with your follow ups to not build a pattern about YOURSELF with your customer.

Like you don’t want to send tons of crappy follow ups such that they start to think “man this guy is really annoying, I’m just gonna auto archive him anytime I see his name.”