Chris Dankowski

Sales & AI Strategist at @Salesloft | Replacing Siloed Systems with Autonomous Engines | Helping Founders Scale Without the Headcount

[Chris Dankowski @cdankowski]

I worked with a woman at HubSpot who was an AE there for 10 years.

She easily could have moved into management but she didn't want to because she absolutely crushed her role due to having a super dialed in process.

One of the main contributors to her success was being able to clearly determine what was real and what wasn't in her pipeline.

This is one of the things she'd do to pressure test her Opps to gain that clarity. 🧵

[Chris Dankowski @cdankowski]

Can we stop putting protein powder in bags? Absolutely horrible UI. Counter ends up looking like Nino Brown's back room.

[Chris Dankowski @cdankowski]

Your first 10 deals closed on founder magic.That doesn't transfer.Document before you hire.

[Chris Dankowski @cdankowski]

When you interview at a new company, they expect you to know their product, their market, and their challenges.

Most reps spend 2 hours on the website and call it "research."

Here's a 30-minute deep prep that'll separate you from every other candidate:

Step 1: Find the company's most recent press release, blog post from the CEO, or earnings call. Paste it in.

Prompt: "What are this company's top 3 strategic priorities right now? What risks or challenges are they publicly acknowledging?"

Step 2: Find the job posting. Paste it in.

Prompt: "Based on this job description, what problems is this team trying to solve by hiring this role? What would 'great' look like in the first 90 days?"

Step 3: Find your interviewer on LinkedIn. Paste their profile.

Prompt: "Based on this person's background, what do they likely value in a candidate? What question could I ask them that would show I understand their world?"

Step 4: Synthesize.

Prompt: "Now give me 3 things I should say in this interview that would make me memorable — not generic 'I'm a hard worker' stuff, but specific insights that show I've done the work."

That's how you walk in looking like a strategist, not an applicant.

[Chris Dankowski @cdankowski]

The average outbound cadence gets a 1-3% reply rate.

Which means 97-99% of your prospects are ignoring you. And you're okay with that because "it's a numbers game."

It's not a numbers game. It's a relevance game.

Here's how to audit your cadences with AI:

Take your current outbound cadence — every email, every step. Paste the full thing into any LLM.

Prompt: "You are a [target persona title] who receives 40+ sales emails per week. Read this sequence and evaluate each step on: (1) would you open this email based on the subject line, (2) would you read past the first sentence, (3) is there a clear reason to reply, (4) does each step add new value or just repeat the ask. Score each email 1-10 and tell me which ones to cut, rewrite, or keep."

Then the fix:

"For the emails you scored below 6, rewrite them. Rules: under 75 words, lead with an insight not a pitch, and the CTA should require less than 30 seconds of the prospect's time."

Run this audit quarterly. The sequences that worked 6 months ago are probably stale today.

Systems beat hustle. Optimized systems beat everything.

[Chris Dankowski @cdankowski]

If you couldn't be in sales tomorrow, what department would you transfer to? Think about it. Then click the link below to make it happen.

[Chris Dankowski @cdankowski]

Leaving sales without a plan is a disaster. I built a 1:1 sprint to engineer your exit. Only taking 5 people. Check the link below.
https://t.co/Y5XwRzUVtQ

[Chris Dankowski @cdankowski]

"Just checking in" is dead.

Use this prompt instead:

"My prospect went dark after a good demo. Give me 3 follow-up options: (1) share a new insight, (2) reference a change in their industry, (3) offer a low-commitment next step that isn't a meeting. Under 75 words each."

Every follow-up needs a reason to reply that isn't "because I need you to."

Kill "checking in." Replace it with a system.

[Chris Dankowski @cdankowski]

After a discovery call, most reps do one of two things: celebrate that it went well, or cringe that it didn't.

Neither makes you better.

Here's a 5-minute post-call debrief that compounds over time:

Right after the call, brain-dump everything you remember — what they said, what you asked, what surprised you, where you stumbled. Don't organize it. Just get it down.

Then paste it into any LLM:

Prompt: "I just had a discovery call. Here's my raw brain dump: [paste]. Analyze this call as if you were my sales coach. Tell me: (1) what was the strongest moment in this call and why, (2) where did I leave value on the table — what should I have asked or explored deeper, (3) based on what the prospect said, what's their real priority (not just what they told me), and (4) what should my follow-up include to move this forward?"

Do this after every call for 30 days.

You'll start seeing patterns in your own selling. Where you rush. Where you don't go deep enough. Where you assume instead of asking.

That's not AI replacing your skills. That's AI accelerating your skills.

[Chris Dankowski @cdankowski]

@steveonomics Along these lines, why are kettlebell folks always fat? I'm talking the ones who are exclusively kettlebell and hardcore about it.

[Chris Dankowski @cdankowski]

How to reverse-engineer a competitor's messaging in 20 min:

1. Copy their homepage + product page + one case study
2. Paste into any LLM: "Who's their ideal customer? Core problem they solve? Primary differentiator? What are they NOT saying?"
3. Now paste YOUR messaging: "Where do we overlap? Where do we differentiate? Where's the gap?"
4. "Give me 3 talk tracks for when a prospect says 'we're looking at [competitor].'"

Competitive intel that marketing takes weeks to produce. You just did it in 20 min.

[Chris Dankowski @cdankowski]

The best sales content doesn't come from marketing. It comes from customer conversations.

Every week you're having calls where buyers tell you their problems, their fears, their language. And it disappears into your CRM notes.

Here's how to turn one customer call into a week of content:

After a great call (or even a tough one), do a brain dump of the key moments. Then:

Prompt 1 — Extract the insight:
"Here's a summary of a call I had with a [title] at a [type of company]. Pull out the single most interesting insight — the thing that would make another [same title] stop scrolling and think 'that's exactly my problem.'"

Prompt 2 — Turn it into a post:
"Now write a LinkedIn post based on that insight. Rules: start with a hook that creates tension, tell the story without naming the company, end with a practical takeaway. Match this tone: [paste one of your existing posts]. Keep it under 200 words."

Prompt 3 — Repurpose:
"Now give me a Twitter/X thread version (5 tweets max) and a one-paragraph version I could use in an email to prospects in the same industry."

One call. Three pieces of content. Fifteen minutes.

You're already doing the hard part — talking to buyers every day. Now capture it.

[Chris Dankowski @cdankowski]

Signal > Spray.

Export your last 20 closed-won deals: industry, size, tech stack, trigger event, cycle length, ACV.

Paste into any LLM: "What patterns do my best customers share? Create a 1-5 scoring rubric."

Now score 10 current prospects against it.

You just built a free ICP model.

Hustle isn't calling everyone. Hustle is knowing which 20 accounts matter.

[Chris Dankowski @cdankowski]

https://t.co/0sIhr9gQQF

[Chris Dankowski @cdankowski]

Most sales reps think about their career like a ladder: BDR → AE → Senior AE → Manager → Director.

Straight up. One rung at a time.

But the reps who build the most fulfilling, highest-earning careers? They think about it like architecture.

What's the foundation? (Core selling skills — discovery, negotiation, pipeline management.)
What's the structure? (Industry expertise, technical knowledge, network.)
What's the design? (The unique combination that makes you un-replaceable.)

Here's a prompt to start thinking like an architect:

"I'm a [current role] with [X years] of experience in [industry]. My strengths are [list 3]. My career goal in 5 years is [goal]. Help me identify: (1) what skills I need to build in the next 12 months, (2) what experiences I should seek out even if they don't come with a promotion, and (3) what makes my profile unique vs. 1,000 other people with my same title."

Stop climbing. Start building.

[Chris Dankowski @cdankowski]

Signals it might be time to leave your sales job:

→ You can't name a new skill you've built in 6 months
→ Your best work doesn't get noticed
→ You're managing around your manager more than building your book

But before you quit, try this:

"I'm considering leaving. Here's what's bothering me: [specifics]. Help me separate: (1) things fixable with a direct conversation, (2) structural things that won't change, (3) things that are about me, not the job."

Don't rage-quit. Think like a strategist.

[Chris Dankowski @cdankowski]

Comp plans are designed by finance. They're optimized for the company, not for you.

That doesn't mean they're bad. It means you need to understand the math before you build your strategy.

Here's a move most reps never make:

Take your comp plan document — the actual PDF or doc, not the summary your manager gave you — and paste it into any LLM.

Prompt: "Break down this compensation plan in plain English. For each component, tell me: (1) what behavior it rewards, (2) what the realistic upside is at 100%, 120%, and 150% attainment, (3) where the biggest accelerators kick in, and (4) what most reps would overlook."

Then follow up:

"Based on this plan, if I could only focus on TWO things to maximize my earnings this year, what would they be? Show me the math."

Most reps grind evenly across all metrics. The top earners know which lever pays 3x and they over-index there.

Your comp plan is a cheat code. You just have to read it like one.

[Chris Dankowski @cdankowski]

Feeling stuck in sales and ready to leave but unsure what's next? Try this simple paper exercise: dump everything you hate about sales. This clarity can save you time and money.

[Chris Dankowski @cdankowski]

I'm opening my Leave Sales program to 5 reps who are ready for a new career. DM me for details

[Chris Dankowski @cdankowski]

Your closed-lost deals are a dataset, not a graveyard.

Export 50 of them. Paste into any LLM:

"Group by loss reason. For each group: what stage do we lose, what patterns exist, what could the rep have done differently?"

Teams I work with cut loss rates 15-20% doing this quarterly.

Your CRM is a coaching tool.

[Chris Dankowski @cdankowski]

The moment you make a sales hire, stop selling.

I know. That's terrifying.

But if you don't, two things happen:

1. Your salesperson never learns to sell independently

2. You become the unofficial backstop for every deal — which means you still have a one-person sales org, you're just paying someone to shadow you

The founder who "stays involved" in deals is the founder who never actually scales.

Here's the hard part: you can only stop selling if there's a system that runs without you.

That means before you hire, you need to extract yourself from your own sales process.

Turn your intuition into written process.

What signals tell you someone is a real buyer vs. a tire kicker?

What objection kills 80% of your deals — and what kills it back?

What's your opening question that gets people talking?

What story do you tell that consistently makes people lean in?

This is your playbook. It lives in your head right now. It needs to be on paper.

Try this:

"I'm going to describe a sales call that went well. Ask me questions to extract: the buyer's signals, the questions I asked, the objections I handled, and the moment they decided to buy. Then synthesize it into a repeatable call framework."

Do this with 5-10 of your won deals. The patterns that emerge are your playbook.

Your first hire shouldn't be figuring out how to sell your product. They should be executing a motion you've already proven works.

The faster you get out of the way, the faster you find out if your system scales.