Founder @MSP Consulting | Enterprise Sales for Startups | $2M => $10M ARR

Most founders aren't bad at sales. They’re just alternating between winging it and following playbooks that were built for companies 10x their size.

I never planned on a career in sales (I studied international relations). But when I fell into sales I realized it was the same skill…understand a situation deeply, then tell a persuasive story around it.

The further I got, the more I kept seeing the same thing. Companies hit the same walls at the same stages and made the same (avoidable) mistakes. And most of the advice for founders was either way too complicated or built for someone else's business.

I didn't want to manage bigger teams at bigger companies. I wanted to help founders solve those problems before they burned 12-18 months figuring it out the hard way.

I work with B2B SaaS founders between $1M–$10M who are building enterprise and midmarket sales orgs. I help them cut through the noise, find the highest-leverage fix, and build something repeatable — without overcomplicating it.

No generic advice or playbooks borrowed from $500M companies. Just proven frameworks built for your stage. 

Book a strategy session below. You’ll leave with clarity on the biggest thing slowing you down right now, and how to fix it.

Monica Stewart

Currently building Starbridge, the GTM Intelligence Platform for businesses selling to government & education. We help our partners leverage industry-specific buying signals - such as strategic plans, board meeting notes, budgets, grants, competitor contract expiration dates, and more - to build a tailored, outbound strategy that drives pipeline.

Before Starbridge, I led sales at Parchment on a journey to $100M in ARR selling to K12 districts, Higher Ed, and state governments before being acquired by Instructure. While at Parchment, I lived the challenge of selling to government and education entities. With the proliferation of spray-and-pray outbound, that challenge has only gotten harder.

I’m helping build Starbridge to simplify selling to government and education. We’re making it easier for businesses to access public contracts and compete on the merits of the product. Our goal? To catalyze a new era of public-private partnerships that change the world for the better.

Matt Stinson

10 AEs, $1M booked in 30 days, and systems that operate like a company 3X our age. We ended last year on an incredible streak. Here are top wins and lessons from Starbridge's biggest month to date.
 
3 Wins:
1.) We booked $1M in a month for the first time in company history. We're now in the top 0.1% of companies historically when it comes to revenue growth at our stage.
 
2.) We've gone from 5 to 10 AEs. Dan, Sam, Nicole, then added McKay, Zac. Now, we've added Bobby, Paige, Steven, Simone, and Patrick. They're all incredible people with energy and contributing from day one.
 
3.) Our systems structure is maturing well beyond our real age. Big shout-out to Jordan, our COO, for spearheading this transformation.
 
3 Learnings:
1.) Never compromise on hiring
After meeting with hundreds of people, I've learned never hire someone unless the team has absolute conviction that we would be at a loss if we didn't bring this person into the org. Maintaining a .1% talent bar is the highest leverage activity I can help support as a leader in the business. 
 
2.) Reframe fear to optimism
I often operate from a position of fear mitigation, playing not to lose. I always think about what will go wrong versus what if all of these things are going right? Justin challenged me to bring my most aggressive, optimistic view and ladder back into what we need to accomplish that. All I can say is, Game On.
 
3.) The power of customer on-sites
We should continue hosting in-person events with customers. The feedback was incredible from our holiday party and our mini-onsite, with people saying how invested they feel in us. People have hours to give you in person versus virtual meetings where they're off and on.
 
To end up where we are and have booked a $1M month at this stage is unfathomable. It's an incredible testament to the product, market fit, and the problem we're solving for our customers.
 
2026 will be the year of Bridge Builders... and I can't wait to meet more of you.

Matt Stinson💫

A comment on my "80 hours a week grind" post stopped me cold.
 
A woman shared her experience growing up as the daughter of a Microsoft employee in the 80s and 90s. It was a time when everyone bought into the mission of “changing the world.”
 
Her mother loved the work. But that devotion often meant choosing the mission over being home.
 
Now, as an adult, the daughter doesn’t celebrate that dedication. She grieves the moments she never got to share with her mother.
 
That really struck me hard.
 
Am I trying to have my cake and eat it too? Can you be a really successful executive at a fast-growing company that demands a lot of you, AND be a really great, present dad?
 
I learned work ethic from my own dad. He was a contractor who came home every day with a broken back and bloody knuckles. I have negative feelings about him missing Saturday games. But I also learned a ton from watching him grind.
 
Unequivocally, being a present dad matters way more to me. But professional success makes that possible - flexibility, financial freedom, and the ability to show my kids that hard work is important and doesn't come easy.
 
I don't know too many people I look up to as role models who are doing both well.
 
I just finished reading Bob Iger's "Ride of a Lifetime." Midway through, he casually mentions getting separated from his wife.
 
Of course he did. He was working 75-80 hours a week at ABC, then Disney.
 
The people who reach the highest levels made very clear choices. They went almost 100% in on career or family.
 
Just be realistic with yourself about what you can and can't do. Because there are sacrifices to make on both sides.
 
What I'm learning is that there will be some things I might miss as a dad that I'll never get back. And there will be things I won't be able to do as a leader. I just have to figure out what those things are.
 
There are no easy answers here. But pretending you can do it all at 100% without making hard choices is dishonest to yourself, your family, and your team.

Every comp plan has this clause: "Management reserves the right to make modifications as they see fit." NEVER ever use it.
 
CROs need to stop any nitpicky argument battles over compensation deals. It’s so penny-wise and pound-foolish.
 
I recently interviewed 3 or 4 AEs who said, "Yeah, I didn’t get paid. It was the first chink in the armor."
 
And I’ve heard so many other stories of reps not getting paid their full commission because it was "too big of a deal."
 
Sure, adjusting the payout may save $100,000 or $200,000 right now. But it burns leadership credibility with your AEs.
 
So while that clause is in there, build the comp plan so that there’s always alignment between incentives.
 
I know people are worried about efficiency and growth at all costs. But pay your sales reps what you told them you'd pay.
 
Even if it's a massive check...pay them the massive check.

Behavioral questions when interviewing salespeople are stupid.
 
I've interviewed 100+ sales reps in my career. Most of the questions that get asked during an interview add very little value to the actual evaluation of that candidate.
 
Sales reps are all good actors to some degree. They are so good at knowing the test and giving you the answers you want to hear. 
 
In my experience, the number one predictor of success for any candidate is whether someone you know or trust has said that this person is elite at what they do. 
 
That's why at Starbridge, we really prioritize references...especially references the candidate didn’t hand-pick.
 
If I can't find people who are ravenous fans of this candidate, I don't hire them.

I used to swear by upfront contracts. Sure, the Sandler Method worked great in 2010. But it's 2026. Now I think they need to be retired.
 
You know the drill. You begin a discovery meeting with a very prescribed structure: Set the agenda, confirm the time, confirm mutual potential outcomes, then bring up your biggest concern.
 
The idea was to get the prospect to psychologically buy upfront. If there's a fit, then schedule a next step. But I think it's gotten so overused over the last decade that it feels like a relic.
 
So much has shifted. Buyers come to meetings having done way more homework and research. They're prepared and know what they want to explore.
 
What bothers me about it now is that it feels like I'm doing something to deceive you. I'm making you commit even though we haven't even talked yet. And I asked for the meeting.
 
It's very transparent when tactics are being used. Especially when you're selling to salespeople who know the playbook. It just doesn't make sense anymore.
 
Look, there are still good elements. Confirming you've got a hard stop at the 30-minute mark, making sure you understand their calendar, overall framing of the call - that's just being professional and respecting their time.
 
But the psychological manipulation at the core of it? That needs to go.
 
I know a lot of people will have different takes on this. So I'd be open to hearing why I'm wrong.

"I'm blown away." This is real feedback from Zachary Oxman, VP of US SLED at Abnormal AI, after our kickoff last week.
 
Getting to lead a revenue team that sells a product that elicits feedback like this is incredible.
 
Knowing that our product will enable Zach's team help more schools, universities, and governments protect against cyberattacks is what it is all about.
 
If you want to be blown away, too, drop me a DM.

I'll be honest. Not every company should use Starbridge. But the customers who get the most out of it share the same 3 characteristics.
 
Characteristic #1: They are open to experiment
Not only do our customers run the core plays like most teams, they're also thinking about their business and use cases. Because of this, they're coming up with novel ideas and building them.
 
Characteristic #2: They have real internal ownership (the “Bridge Builder”)
With our top customers, there’s someone in sales leadership or revops who’s a systems thinker. They partner extremely closely with our CSA team to create and effectuate what matters most to their business.
 
Characteristic #3: They actually add value to the market
Our best customers have a product or service that solves a real problem. Someone has to theoretically want what you offer. Then, we can help you get in front of more of those people. 
 
A lot of prospects will come to us and say, "Man, our sales suck." So we ask them, "Tell us why you're different? Why are you winning?" And they can't explain why.
 
If you can’t figure out why someone would want your thing, we’re not going to help you win more.
 
We can't help you create product market fit. But we can help you exploit it.

This used to be my reality: 2-3 promising conversations with a customer, only to find out that their budget is frozen or there's no appetite for innovation. I’d spend hours on the phone or prospecting before learning what I should’ve known day one.
 
Me: "Great discovery call. Awesome demo with stakeholders. Let's talk budget."
Prospect: "Budget's down 15%."
 
Cool. Glad we wasted all this time.
 
With Starbridge, I don’t even start with a call. With our new budget trend data feature, we now rank propensity to spend, so I put them in some other drip campaign right away.
 
We run a thorough analysis up front on whether or not an entity is likely to spend in a given category. I filter my accounts by that data initially, versus finding out about it hours later.
 
This is the kind of insight that significantly influences where I'd be spending my time as a sales rep and where I wouldn't. It's changing how public sector sales teams operate.
 
If you're selling into government or education and want to see how this works, let's talk.

Every revenue leader wants growth coming out of SKO. But actual growth depends on the coaching habits that follow. 
 
While SKO is usually treated like a once-a-year event, the goal of an SKO is to accelerate growth and jumpstart learning.
 
The problem is that most teams expect those outcomes to come from 3 days of sessions that try to wrap together 12 different topics.
 
You might tease out 1 or 2 things. But without a system to reinforce them, the learning fades, and behavior doesn’t really change.
 
The way you accelerate growth and learning is through continuous improvement and feedback.
 
This became painfully obvious when I wasn't physically there on the final day. I could see that people looked confused, but I couldn't grab them afterwards and talk through it.
 
That moment reinforced something I already suspected: The real value of SKO is everything that happens outside the sessions - the getting to know people, connecting with them, and creating energy together.
 
So while we’ve done an okay job of this as a business last year, this year, we’re being much more intentional.
 
Going forward, we’re building off SKO momentum with one-hour weekly coaching calls for the entire revenue team.
 
In these sessions, we’ll do film review, role play, and break things down into very discrete, bite-sized pieces so the team can actually absorb and apply the learnings.
 
In this way, we’re training and building the muscle of expecting feedback, getting that feedback, and integrating it.
 
That shared context and trust are what will allow learning to stick once everyone is back in their day-to-day work.

When you start closing deals with the biggest players in K12, you know something's working.
 
That's why we're so honored that Frontline Education chose Starbridge to fuel their GTM strategy.
 
We're stoked to support Frontline's mission to empower K12 leaders. And we're grateful they're betting on us to help them win more deals.
 
See more of our amazing customer stories on our website. (Link in the comments)

taplio

The Battle

Monica Stewart

Matt Stinson

Followers

Posts

Engagements

Likes

Performance ScoreMatt Stinson's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Monica Stewart

Matt Stinson

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Matt Stinson's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreMatt Stinson's LinkedIn Performance