Fixing the deals that get stuck

This is the first installment of our Partner Interview Series, where Gabe sits down with the people who help advisors and sales teams run their business, and gets into where AI fits into that today.

First up is Duston Harper, founder of Groundplan Co., a sales consulting and AI implementation practice. Duston built the SalesOS Blueprint, a two-week assessment that diagnoses where complex deals get stuck, where reps are wasting the most time, and hands clients a concrete plan to fix both. He spent his first decade in sales at Milwaukee Tool, then moved into medical device sales at Stryker, where a steep learning curve pushed him to get serious about mapping how companies actually buy instead of just how salespeople want to sell. He's also a Quin customer himself, and has started bringing Quin into his own client work.

Tell us about Groundplan. Who do you work with, and what's the core problem you solve?

The main two problems I focus on are, one, complex deals getting stuck. When you're in enterprise sales or bigger deal sizes, six figures plus, there's a lot of people involved, month-long sales cycles, a lot of approvals that have to happen, and it's easy for deals to get stuck. That's where people get ghosted, they lose to the status quo, and it causes a lot of frustration for the C-suite, the sales leaders, and the reps, because people aren't closing deals and the pipeline stalls.

Secondarily, and related to that, is freeing up time. Salespeople and producers really shouldn't be doing administrative work. That should be behind the scenes, so I try to automate some of that to get them better at closing deals and get them more time in front of the customer.

It tends to be more laggard industries, med device, med tech, industrial, manufacturing, insurance. It's pretty consistent and industry-agnostic. I've been in sales my whole career across several industries, so I can relate to a lot of these places, and I still sell myself as a founder. I'm a consultant with my own agency, still dealing with these same big deals and automation behind the scenes, so I think that gives me credibility when I'm talking to people.

A lot of our audience is in financial services. Do you think this is the same for financial advisors and insurance agents?

The complex-deal part is definitely relevant there, probably more on the commercial side or bigger contracts. Some of the day-to-day stuff is a shorter, more transactional sales cycle. But I have coaching clients in financial advising, and everything we're talking about is very relevant, especially the administrative side. The amount of email triage, back and forth, and CRM clunkiness, pretty much every practice owner or producer is drowning in it, and they want to fix it because ultimately they want to be in front of the customer. If they're burnt out from doing all the admin work, it doesn't go as well. They can get away with it for a while, but eventually, over years, it starts dragging people down.

How did the sales process become the focus for you?

The first decade of my career, I worked for Milwaukee Tool. Amazing run, seven different roles in sales and leadership, and the company was blowing up. But things came kind of easy, there was a lot of momentum and brand recognition. I decided to change industries and went to Stryker in medical device, and I was probably a little overconfident going in. I quickly realized healthcare, selling to hospitals, dealing with the clinical and business side, is super complex. You're talking twelve-month-plus sales cycles, and I had to rebuild my credibility in a new industry.

I got humbled a bit, and I wanted to get better, so I found a course called the Maverick Method, from a guy named Brian Burns. It's all about how companies make decisions and mapping your sales process based on how they buy, not how we want to sell. That really resonated with me in healthcare. Once I became a student of it, I started seeing a lot of success, forecasting better and closing more deals. I've used that method across industries since, big companies and startups.

Most people hear a lot about gimmicks and tricks for closing deals, but in a complex sale you're building up over months, that stuff doesn't work. You have to think more like a project manager or an architect. What I found across every industry I mentioned is a very common problem. People get ghosted or lose to "no decision," but they didn't really lose it in that moment, they lost it two or three months earlier because they fell into a trap. I'll give you an example. Someone asks for a proposal, and it feels good to send one. But if you're not the incumbent or a big brand, and you haven't established your value first, all they see is a number on a piece of paper, with no reason to talk to you. Preventing those traps is what it's all about.

What are the most common traps you see founders and sales leaders running into? What are your top three?

We call these sales traps. I'm talking about complex deals here, not transactional, same-day sales.

The first one I mentioned is the proposal trap. You're probably getting tasked by your company to send out proposals, and it feels good, it's tracked. But if you haven't gone over the ROI or the value versus price, and they don't understand how you're different, sending a proposal is probably going to set you up for failure, especially if you're not the incumbent or a well-known brand. They'll just see a number on a page and go with the cheapest option or the incumbent.

The second is being single-threaded. It's like dating. You get comfortable with the person you're talking to, you have good rapport, but a lot of times that person has no decision-making authority internally. You're negotiating with somebody who can't even get the deal done, while there are ten other people involved behind the scenes. Early on, you have to multi-thread and figure out what this looks like from both a business and a technical side. It's uncomfortable, it can feel like you're going behind your champion's back, but the longer you stay single-threaded, the harder it is to get out of it.

The third one is so simple, getting the next step on the calendar before the call ends, not just talking about it. You have to be diligent up front about what a realistic next step actually is, a demo, a review with the CFO, whatever it is, and then be good at presenting it, because everyone's busy and nobody wants to commit. You'd be shocked how many salespeople don't get that next step booked. Next thing you know they're checking in, circling back, sending ten emails, with nothing on the calendar.

Do those apply to financial advisors trying to bring on new business and referrals?

For sure. On getting the next step on the calendar, I see a lot of advisors just default to the status quo, a quarterly check-in or a generic report. If you really want to stand out, having a consistent rhythm with your top-tier clients, monthly or quarterly depending on how many you have, has a huge impact, especially if you do something a little different on those calls.

On multi-threading, even if you're dealing with a single decision-maker, there's usually someone else involved. If you're trying to switch someone from an advisor they've used for fifteen years, you probably have to talk to a spouse or significant other too. You want to get ahead of that instead of it coming up and shutting things down at the last minute.

And it's probably easy for agents to just send a quote when someone asks for one. It feels good, and it gets tracked. But if you're trying to get someone to switch from an advisor they're loyal to, a quote by itself usually isn't enough to convince them.

You've put together the SalesOS Blueprint. What is that, and what does the process look like?

I had a great mentor and learned from one of the best out there, and I've used that to build my own version of it for the AI era. I've been around a lot of big consultants, tech and SaaS companies, and AI companies, and it's overwhelming for company leadership. They have so many tools and people pitching them, and it's usually expensive. Some of it is genuinely good, but a lot of times people spend a fortune on consultants and don't see the ROI.

Because I'm more nimble, I wanted to provide as much value as possible in a short amount of time. The SalesOS Blueprint is a two-week sales assessment. First, I go deep on the number one trap where their deals are getting stuck, and diagnose it so they can prevent it. Second, I look at where they're wasting the most time on monotonous tasks, since that's causing burnout and getting in the way of closing deals. Third, I hand them an implementation plan, exactly what I'd do. They're welcome to run with that on their own, or keep working with me if they want help. It's paid, priced so someone at VP level or higher can approve it without a lot of red tape, but they get a lot of value either way.

Let's shift to AI. What's your perspective, having worked with sales teams across industries trying to optimize their process?

It's everyone's favorite topic. I used to be the workhorse. I still work hard, but the first twelve years of my career, I was always grinding, sixty-hour weeks, doing admin work at night. Eventually the workhorse gets tired, mostly because of that admin stuff, emails, PowerPoints, following up on twenty meetings from the week.

Where it changed for me was getting recruited into an AI role-play company a few years back, which really opened my eyes to what AI could do for sales teams and for myself behind the scenes. I'd tried an executive assistant and a virtual assistant before that, but the ramp-up time was frustrating when you're impatient like most salespeople and founders are. In the past year and a half, I started using tools at a higher level, Claude and Lovable for content, since I post a lot on LinkedIn. It was clunky at first, but you have to get in the game and try things.

The past year, going back to being a founder, all that admin work crept back up on me, building a website, follow-ups, meetings. That's when I came across Quin and met Gabe, and it was eye-opening. I think AI conversations focus so much on the big problems that people forget it's really good at the monotonous, executive-assistant-type work behind the scenes. That's what drove me to Quin, and I saw immediate ROI. Now I'd say I'm above average with AI usage, and the biggest time savings have come from stuff like Quin, which has helped me perform better and drive more revenue, for myself and for my clients.

What are your top three favorite Quin workflows, the ones you'd recommend to the clients you work with?

The note-taker is one of the first things that provides a ton of value. You can use it on Teams, Zoom, or Google Meet, and it adds notes behind the scenes, but you can also use your phone for in-person meetings. A lot of the industries I work with are a mix of online and in-person, and there's a real gap on the in-person side, so that's great. It's also good about not giving you too much information, a lot of note-takers dump everything and it's overwhelming, but Quin recaps what's actually important.

The second is email triage and drafting replies in my own voice. When you've got thirty emails and you're already tired and stressed, it's exhausting. So at the end of the day or week, I can just look it over. Sometimes it's perfect and I send it, sometimes I tweak a few things, but it's a huge amount of peace of mind.

Third, and this brings a few things together, I'm big on preparation and follow-through, and Quin handles that well. It gives me meeting prep the day before, so I'm ready without having to think about it. During the call, the note-taker joins and automatically updates my CRM, tasks and key dates included. Then on the follow-through side, the follow-up email gets drafted immediately, and if there's a calendar invite needed, Quin offers to send it. That last one alone saves maybe fifteen to twenty minutes per meeting, and when you've got fifteen to twenty client meetings a week, that adds up fast.

What's been your experience working with the Quin team, through support or otherwise?

There's always some skepticism around AI, and change management is always the hardest part of any implementation. What's great about Quin, and I can personally vouch for this, is that the support is above and beyond. You've got founders like Gabe attending to some of it directly. Any time I've had a question, it's a twenty-four-hour turnaround or less, usually way sooner. That matters a lot in the first few weeks or months of bringing something new on.

On top of that, about ninety-eight percent of questions are already answered in the knowledge base, so you often don't even need to reach out. And Quin runs webinars almost weekly with real use cases and customer stories, comparing Quin to other tools, that actually provide value instead of a pitch. That's rare in this AI race, and it's a big reason I'm a fan of Quin.

Last few questions, just for fun. If you had a magic wand and could have one thing built into Quin, what would it be?

I'm deep on the sales side, so it's going to be sales-related. Those complex deals I mentioned, you want a second opinion, almost like a coach behind you. I'd want a deal score index that grades an entire complex deal in progress against those common traps, catching things maybe before I even do. I've actually already built a lighter version of this in Quin that grades individual calls, but it's not grading the whole deal over time. Being able to score the full deal throughout the process, and catch things like "you didn't get the next step on the calendar" before it becomes a problem, would be huge.

Favorite software or AI tool you're using today?

I'll do a combo, Claude and Quin together. Claude is like my brain, my strategic advisor that pushes back and gives me what I need to know, and then Quin executes. At first I used one or the other, but having both going together has really helped. At this point it's a must-have.

Favorite productivity hack?

I'm big on planning the week and the day. Usually Friday afternoon, sometimes Saturday morning, I plan out my top two or three personal and professional goals for the following week. That way, on Monday, I already know what I want to accomplish, work is usually revenue-focused, personal could be faith or fitness, and I don't have to think as much about where to focus each day. I actually now have Quin help me put that plan together instead of writing it out by hand.

Last one, how do you take your coffee?

I'm a degenerate coffee drinker, four to five cups a day. Usually drip, medium-dark roast, with one Splenda and some half-and-half. I keep it simple with K-cups at home, but I spend a fortune at coffee shops around St. Pete and Tampa, there are so many good independent ones. My favorite is Intermezzo.

Duston's SalesOS Blueprint and the traps he described apply well beyond sales teams. If you want to talk shop with him about fixing a stuck pipeline, or see how he's using Quin day to day, you can find him at Groundplan Co. or connect with him on LinkedIn.