Most sales books will tell you that the way to win business is to pitch the right offer, at the right time, to the right person. After leading community at Huntress and spending years building a sales agency that served hundreds of MSPs, I have a quieter theory. You do not win business across the desk. You win it long before the desk ever comes up.
The desk is where you sign a deal. You won that business somewhere else. You won it at a chamber of commerce event. You won it at a roadshow you put together. You won it because you met somebody in a bar one night and got talking to them.
The mechanics of winning business that way have not changed in a generation. What has changed is that most of those small moments now have to be engineered on purpose. Nobody drops by for coffee anymore. Most partner-facing sellers never set foot in the client’s office. The work that used to happen naturally has to be scheduled, and most MSPs are not doing it.
This post is for MSP owners and sellers who want to play the long game in an environment that is making the long game harder. The principle is old: under promise and over deliver. The execution requires a new playbook.
Why Sticky Relationships Matter More Than Ever
The MSP industry is consolidating. National conglomerates are absorbing regional shops. Private equity is changing the economics of the space. In that environment, the five-person MSP cannot compete on scale, and the ten-person MSP cannot compete on price.
What smaller providers can compete on is relationship. The client who has been helped by you personally, who remembers that you drove donuts out to their office when they had a bad week, who knows your kids’ names, is not going to leave for a cheaper bid. That loyalty is the competitive moat, and it has to be built one interaction at a time.
I frame the work this way: How are you going to be the one that they want to stick around with? Everything that follows is a function of that question.
Look for What No One Else Is Doing
The specific tactics matter less than the pattern. You are looking for the small, repeatable acts that most of your competitors are too busy, too distracted, or too transactional to do.
Remember the client’s birthday. Ask about the wedding their daughter mentioned six months ago. Send a handwritten note when you see their company in the local paper. Drop by, unannounced, when you happen to be in the neighborhood, with coffee and no agenda. If you are a regional MSP with clients in a roughly one-hour drive radius, at least one of those interactions should happen with each client every quarter.
I call the Huntress version of this “surprise and delight.” My team runs an explicit program around making sure that on the worst day, we show up for our partners, and on the best day, we show up for them too. I want to be the forefront in everybody’s mind, whether you’re doing business with us or not. That’s probably the piece Huntress has been really good at.
Notice the move: the point of the program is to be present, with sales as a downstream effect. The sales follow, but only because the presence is real.
Be the Person Who Puts the Card Down
One line from my approach captures the entire philosophy. In community, we strive to be the person who, when someone wants to buy a drink for the bar, we put our card down.
The contrast matters. Some people show up at the industry event, the chamber meeting, the partner dinner, looking around for who is going to pay. Others show up with their card already on the table. Over a long enough horizon, the second group wins. They get invited back. They get introduced. They get the warm handoff.
Applied to MSP work, this looks like a partner who volunteers to host the next meetup without being asked. A seller who refers clients to their own competitors when the fit is wrong, because they know the ecosystem is bigger than one account. A technical lead who answers questions in a peer community for free, without tagging every post with a pitch.
The payoff is cumulative. You will not see it in next quarter’s pipeline. You will see it three years from now, when a client you helped back in year one brings you their cousin’s business, and their cousin brings you two more.
Engineer the Small Moments That Used to Happen by Accident
Remote work has quietly removed most of the informal touchpoints that used to drive relationship building. You do not bump into your client in the elevator. You are not at the same conference coffee break. The weekly lunches are gone.
The move is to put those moments back on the calendar, on purpose. I think about it like this: you sit at a desk from the start of your day to the very end of your day. Gone are the days of getting in the car and driving home and talking the entire way home on different calls because you’re just reconnecting.
Recreate the reconnection on purpose. Block thirty minutes every Friday for a check-in call that has no agenda with a client you have not spoken to in a month. Schedule quarterly in-person visits for every client within driving distance. Send a short video message instead of another email. Put the rubber ducky in the mail, to borrow one of my favorite stories about a Huntress moment that started with a lost toy in a pub and ended with an ongoing relationship.
If you do not schedule it, it will not happen. That is the single biggest failure mode I see among the MSPs I work with. They know they should be doing relationship work. They do not block time for it. And then they wonder why the pipeline looks the way it does.
You Cannot Measure It. Do It Anyway.
The hardest part of under promising and over delivering is that you cannot put a commission number on it. I can tell you that if you don’t do it, there won’t be any luck. And that is the shape of the tradeoff. The activities that build sticky relationships are exactly the ones that do not show up cleanly in a pipeline report.
That is also why most MSPs stop doing them the minute a quarter gets tight. Understandable. Also the wrong move. The quarter you skip the relationship work is the quarter whose pain you will feel eighteen months later, when the pipeline dries up and you cannot figure out why.
The alternative is a discipline. Budget time for relationship work the way you budget time for prospecting. Measure the inputs, not the outputs: how many coffee visits, how many unscheduled check-ins, how many peer introductions you made. Over a year, the outputs follow.
One Experiment This Month
Pick three clients. For each one, identify one small act this month that no competitor would bother with. Do it. Then, at the end of the month, ask yourself which of those clients reached back out on their own.
That is the signal you are looking for.
Cynomi’s GTM Academy Sales Kit includes relationship-building frameworks, quarterly business review templates, and playbooks for putting these motions on your calendar so they happen. If you are ready to make the long game a discipline, you can pick up the kit here.