Chris Dankowski

Mid Market Account Executive

I wear two hats.

By day, I am a Sr. Sales & AI Strategy Consultant at Salesloft, where I help the world’s largest companies (like Verizon, Office Depot, and LinkedIn) modernize how they sell. By night, I am in the lab, designing autonomous revenue engines for founders who can't afford enterprise bloat.

My career has never been a straight line. I started as a painting contractor, knocking on doors and selling jobs to buy my first van. I spent over a decade managing teams and carrying a bag at companies like Evernote, Outreach, and HubSpot.

I’ve seen the highs:

Closing the largest deal in company history at Evernote.

Winning "Manager of the Year" twice.

Helping build BDR orgs for companies like OneMedical and Genetec.

I’ve also seen the lows. In 2020, after years of grinding, I hit a scorching case of burnout. I quit sales with no plan and spent 7 months landscaping my yard and figuring out "What's next?".

That break taught me a critical lesson: Hustle is not a strategy. Infrastructure is.

Since returning, I have pivoted from "Grinding" to "Building."

At Salesloft, I carved out a hybrid role leading internal AI adoption, building agents and prompts to replace manual work.

I earned my certification in Change Management for Generative AI from Vanderbilt University to formalize this shift.

Now, I am obsessed with one problem: Siloed Systems.

Too many founders believe Sales is an "Art." They hire expensive VPs, buy them a quarter zip Patagonia vest, and hope for magic. I believe Sales is a Manufacturing Process. But right now, your factory floor is broken. Your data lives in islands, and your reps are the manual bridges carrying information back and forth.

I am currently developing a framework to fix this:

   - The Input: High-integrity Data (Unifying the silos).

   - The Machine: Autonomous Logic & Infrastructure (Agents, not just Reps).

   - The Output: Predictable, high-margin Revenue.

I focus on two areas:

   - Enterprise Strategy (via Salesloft) for leaders deploying AI at scale.

   - Sales Infrastructure (My current build) for early-stage founders who need to validate their GTM motion before hiring a VP.

I’m currently building and testing these workflows in public. If you believe that the future of sales isn't "More Reps," but "Better Plumbing"—follow along.

Something new is on the horizon.

Sales Trainer and Career Guide for sales professionals

1:1 career guidance for sales reps who are looking to advance their careers, or pivot out of sales into a new career.

Also freelance as a part time sales trainer at tech sales boot camps including Flockjay, Springboard, and Always Hired.

If you're in sales, and are having a tough time finding your stride, don't give up on yourself.

There are two drivers of success...

What you do, and where you do it.

The number of sales orgs with inadequate leadership, resources, PMF, etc far outnumber companies with the right cocktail of attributes to put you in a position to succeed.

I've seen top-shelf reps struggle with a bad territory.

I've seen mediocre sellers make P-club in the right environment.

I once talked to Strategic AE with multiple 7-figure W2s who was let go not once but TWICE for performance.

If you want to stay in sales but are struggling, get real specific about what you need to be successful, and then go about finding that.

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

"So, why did you leave your last job?"

If you were fired or put on a PIP, this question is terrifying.

You want to be honest, but you also want to say: "Because they had no idea what they were doing."

I was coaching a client who had a rough stint at a major tech company. 

He was hired for inbound, the inbound dried up, he tried to go outbound, and management shut him down.

Here is the script I gave him to turn a "Red Flag" into a "Green Flag":

"I joined at an interesting time. During the interview, the expectation was that I would hit quota based on inbound demand. When I got in the seat, the reality was different—the inbound had dried up. I did the math and realized I needed to hunt, so I started building an outbound motion. Unfortunately, leadership hadn't defined their outbound strategy yet and asked me to stand down. I was in a position where I wasn't given the fuel to drive the car, and I wasn't allowed to go get my own gas. So, we decided to mutually part ways."

Why this works:

- It’s objective, not emotional.
- It shows you know "Sales Math."
- It shows you tried to solve the problem.

Dude, the "Forecast Call" is the weirdest tradition in human history.

It’s like... we all get in a circle on Zoom and just guess the future together. 

It’s fortune telling, but with spreadsheets and Patagonia vests.

Your manager is like, "Hey man, is that deal gonna close?"

And you’re like, "Yeah, I feel good about it."

You feel good? Based on what? The vibes?

Did the client say yes? No.

Did they sign the contract? No.

But they opened your email twice on a Tuesday, so now it’s "Committed."

We’re just selling imaginary numbers to people who are pretending to believe us.

It’s a wild hustle.

Sales Career Advisor ~Sales & AI Strategist at Salesloft ~Alum of Evernote, Outreach, and HubSpot

There is a lot of gaslighting in sales toward folks who prioritize base salary.

"Aren't you confident in your ability?" they ask.

I am.

But I'm not confident in your quota setting abilities.

I'm not confident in your market conditions.

I'm not confident in your data quality.

And frankly, looking at your Glassdoor reviews, I'm not confident in your churn rate.

Stop letting hiring managers make you feel guilty for looking out for #1.

In this economy, OTE is a fantasy until proven otherwise. Base salary is rent.

In my new Career Playbook, I included a full section on "Offer Negotiation."

Grab it in the comments below.

Just bought a $497 "AI Sales Mastery" course from a 24-year-old Life Coach.

Here is what I learned:

- Open ChatGPT.
- Type "Write me an email."
- Hit enter.

Groundbreaking stuff.

The "AI Guru" industry is a dumpster fire right now.

Everyone is an expert because they read a thread on Twitter.

You don't need a course. 

You don't need a certification.

You just need to open the tool and start asking it questions about your job.

Save your $500. Buy some groceries. 

Just use the free version and get to work.

Your LinkedIn profile is not a resume. It is a Search Engine Optimization (SEO) project.

Recruiters do not read profiles. They use software to scan for keywords.
I
f you don't have the keywords, you don't exist.

I was reviewing a client's profile who was struggling to get inbound interest. 

His "Skills" section was empty.

The Fix (The "Juice It Up" Method):

Go to the "Skills" section under every single job you have listed. You can add up to 50 skills per role.

Use all of them.

- Cold Calling
- SaaS
- Salesforce
- Closing

Don't be shy. If you touched it, list it.

You aren't trying to impress a human (yet). You are trying to trigger an algorithm.

Voice-to-Text is the most underrated tool.

I have my best ideas when I'm walking.

By the time I get back to my desk, they're gone.

I set up a workflow:

- I record a voice note on my phone.
- It auto-transcribes.
- It gets shared to NotebookLM.
- Once a week NotebookLM summarizes all of my voice notes into bullet points.

I wrote this post while walking my dog.

Capture the flow when it happens.

AI isn't going to replace sales reps.

But a sales rep using AI is definitely going to replace you.

I hear the panic every day.

"Chris, is ChatGPT going to steal my job?"

Let’s be real. If your job is sending generic, templated emails and reading a script... yes. You are cooked.

A robot can do that faster, cheaper, and without complaining about the 401k match.

But if your job is:

- Building trust.
- Navigating complex politics.
- Understanding human emotion.
- Closing the deal.

Then AI is not your enemy. It is your Exoskeleton.

Stop fearing the tool. Learn how to hold the hammer.

I see reps using ChatGPT to write "Happy Birthday" emails.

It’s like using a Ferrari to go to the mailbox.

You are sitting on the most powerful sales assistant in history, and you're using it like a spell-checker.

Stop asking: "Write me an email."

Start asking:

"Act as a VP of Finance. I am selling you [Product]. What are the top 3 objections you would have to this price point, and how should I overcome them?"

I compiled 61 prompts like this one into a cheat sheet.

The B2B SaaS AI Prompt Library.

Free download in the comments.

Sending a proposal is not "selling."

It's just admin work.

Getting the signature is selling.

I was reviewing a client's pipeline. He had 8 proposals sitting out there.

"I don't want to bug them," he said.

Here is the reality: Your quote is dying in their inbox.

You need a system to keep it alive.

The "Quote Assembly Line" Sequence:

- The Setup: When you send the quote, tell them: "This pricing is valid for X days." (Create urgency).

- The Automation: Enroll them in a 20-day sequence immediately.

-- Day 3: "Just checking if the PDF opened correctly?"
-- Day 6: "Any questions from Legal?"
-- Day 9: "Just a reminder on that X-day pricing expiry."
-- Day 12: "Do we need to adjust the scope to get this signed by Friday?"

Stop relying on your memory to chase money.

Automate the nag. 

If they don't sign, at least you get a "No" so you can move on.

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