Connect With Maggie Wymore from ServiceTitan
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Why Year-End Reviews Matter
Maggie Wymore:
Most unique ways that we can leverage AI in the landscape space is specifically tied to making the everyday account manager's job more streamlined. One area I feel like AI can really be utilized and Aspire is doubling down, is making increasing those opportunities for enhancement sales by automating that site audit process. But if you're not providing client budget worksheets to your people, when you're having the renewal conversations and really sitting down and having a human conversation, you're missing out.
Maggie’s Role At Aspire Software
Jack Jostes:
Hey, it's Jack Jostes and welcome back to the Landscaper's Guide podcast. Today I'm excited to interview Maggie Wymore from Aspire Software. Maggie, how are you doing today?
Maggie Wymore:
I'm good, how are you, Jack?
Jack Jostes:
Good, good.
Maggie Wymore:
Thank you for having me.
Jack Jostes:
Yeah, thanks for coming. So we're wrapping up 2025 and what are some of the things that you're kind of coaching Aspire clients on or that you'd want landscape companies to think of to really button up their financials for the end of the year?
Cleaning Up Financial Data Before Year-End
Maggie Wymore:
Yeah, it's a great question. There's a couple of things. Obviously I grew up in the industry and you know, we all feel the seasonality of the industry, but if you are looking to close out your year, adjust things, the first thing I would look at is just like the health of my contracts as I'm going into next year and am I setting my team up for success?
And that starts with just reviewing those high end financials. I'll get a little bit more into the contract side of things. But as a landscape owner, you want to make sure when you're reviewing your year end financials so your long term plan in mind.
So what does your 2026 look like? Do you plan on buying a company? Do you plan on selling your company? Do you plan on getting some private equity investment?
And are your financials set up to make yourself look desirable?
If you're just kind of looking to keep status quo and just kind of run another year as a landscape company, what are your growth goals? How are you investing in sales?
Like everything that you provide, Jack, in the sales marketing space, I think it's important to look at what strategies you are going to double down on next year? What parts of your business are operating at a healthy level.
So if it's your fertilization part, if it's your snow removal, which we all can't depend on snow, really understanding down to that service line where you are making money and where you are losing money.
Evaluating Profitability By Service Line
Jack Jostes:
I like that. So really running like, do you mean running a profit and loss by department or how would you do that?
Maggie Wymore:
Yeah, you can do that. You have to start, dial it back a little bit, and you have to start with the inputs.
So as you're going into the last month of your year, I would actually go back and get your hands dirty and review every single job to make sure there's nothing left behind, there's no cost not associated with it, your teams are operating in the correct rhythm so that when you do get to that point where you're reviewing your P and L and drilling it down to a monthly basis, a service basis, however you want to dissect it based on your goals, you have the right inputs.
Because data and results that you get out of data are only as good as the inputs.
Maggie’s Background In The Green Industry
Jack Jostes:
So Maggie, you mentioned that you grew up in the industry. I know that you've worked at Aspire for like eight or nine years now, is that right?
Maggie Wymore:
Yep.
Jack Jostes:
So tell us a little bit about your background.
Maggie Wymore:
Yeah, for sure. So my first job in the industry was when I was 14. I've always been ambitious. In high school, I told my parents I wanted to get a job at a local nursery and landscape company outside of Chicago in a small suburb. It's called Harms Farm and Landscape.
Jack Jostes:
Which suburb?
Maggie Wymore:
It was in McHenry, Illinois.
Jack Jostes:
Okay. I'm from Arlington Heights, Illinois.
Maggie Wymore:
I was born in Arlington Heights, so I'm very familiar with you.
Jack Jostes:
I was born in Arlington Heights, probably.
Maggie Wymore:
Same hospital.
Jack Jostes:
My first job was working at Pesche's Flowers in Flames.
Maggie Wymore:
Exactly where that is. Yeah. So that's awesome.
From Account Manager To Aspire
Maggie Wymore:
It was a small company. It's called Harms Farm. It was a family owned business. It was watering plants in the greenhouse, weeding, helping with the cash register, potting, doing things like that.
And then when I went to college, I decided to go into engineering. Quickly realized that I'm too much of a people person and I didn't want to stay in engineering, so I switched my major to horticulture.
I graduated from the University of Illinois with a degree in horticulture, emphasis in production and management.
Outside of college, I moved to a large commercial landscaper up in the Chicagoland area to do an internship and then work full time. That company was called Acres Group. They're now a Yellowstone company.
Then when I got married, I moved down to St. Louis and worked for a small landscaper there, Dowco Enterprises.
I found myself wanting to make a bigger impact on the industry. I had just had my first child and was ready to take on more.
Aspire Software is local to St. Louis, where I lived, and I came on very early in their journey. I was the 23rd employee and have been there ever since and could not be happier.
Why Maggie Stayed At Aspire
Jack Jostes:
So what about Aspire keeps you there?
Maggie Wymore:
What keeps me there is the customers, because I was a customer. I was the end user of technology in the landscape industry, and I saw what great impact it made to me when I was an account manager and a salesperson.
When ServiceTitan acquired Aspire back in 2021, I saw a significant increase in investment in making our customer experience better. To this day, it's incredible.
The founders of ServiceTitan and the founders of Aspire share the same vision, which is putting customers first.
Selling More Enhancements
Jack Jostes:
Speaking of enhancements, what ideas do you have to help people listening sell more enhancements?
Maggie Wymore:
Yeah, that's a very loaded question. As someone who used to carry an enhancement quota against my maintenance portfolio for many years, this is a topic that's near and dear to my heart.
Enhancement Benchmarks And Quotas
Maggie Wymore:
I managed about a $1.2 million portfolio of commercial properties, primarily HOA based, and my quota was to sell at least 70% of that in enhancements every year.
Jack Jostes:
I hear a lot of other commercial contractors targeting closer to 30%.
Maggie Wymore:
I think it depends on what is included in that initial contract.
Using AI To Streamline Site Audits
Maggie Wymore:
One of the most unique ways that we can leverage AI in the landscape space is specifically tied to making the everyday account manager's job more streamlined.
When I was an account manager, I had a large property in my portfolio called Greg's Landing in Libertyville, Illinois. One of the things I did was put together a property report every month.
I shared what was going well, what needed attention, and where there were opportunities. The board loved it. That proactive communication led to renewals and long-term relationships.
Aspire is now looking at how AI can take the site audit process and automate it. If I take a photo and add notes about a tree that needs to be removed, AI can help generate the estimate based on past data so the account manager can review it instead of building it from scratch.
Retention Through Line-By-Line Renewals
Maggie Wymore:
This is where we get lost in the industry. Renewal time comes and people slap a 3% increase across the board.
But when you dig in, you may find mowing is profitable while pruning or fertilization is losing money. Labor hours matter.
Reviewing contracts line by line allows you to say, “I need to increase this service, and here’s why,” which creates a more natural conversation.
Client Budget Worksheets And Renewals
Maggie Wymore:
You should be proactively providing client budget worksheets.
If they decline an enhancement this year, ask if they want it included in next year’s budget.
If you're not providing client budget worksheets during renewal conversations and having a real human conversation, you're missing out.
Final Thoughts And Where To Learn More
Jack Jostes:
For folks who want to learn more about Aspire or maybe if they're even a current customer, where can they go?
Maggie Wymore:
I'm very active on LinkedIn, and you can also reach out to our team directly through our website. Happy to help any way I can.
Jack Jostes:
Cool. Well, Maggie Wymore, we’ll put your LinkedIn in the show notes. Thanks for coming on the Landscaper’s Guide.
Maggie Wymore:
Thanks, Jack. I’d be excited to do it again.
Jack Jostes:
Hey, it’s Jack. If you enjoyed today’s episode, I invite you to subscribe to our YouTube channel, check us out on Apple Podcasts and Spotify, and subscribe at landscapersguide.com/podcast so you never miss an episode. Plus, get invitations to my live and virtual events. I look forward to talking with you next week on the Landscaper’s Guide.