How Winterspring Farm Overcame Uncertainty Through Strategic Marketing
“We're here. We got this. And we have the power to continue.”
Case Study: Website — Marketing — Graphic Design — Meta Ads — Training
Quotes have been edited for length and clarity.
We recently caught up with Roxanne Ramirez of Winterspring Farm to learn about the history of the business she runs with partner Caleb Trainor and how beginning a relationship with Grapevine helped them achieve:
30% sales increase
year over year
Sold out CSA
2 years in a row
Sold out Seedling Sale
Starting a business during unprecedented global uncertainty.
Winterspring was founded in 2020, in the midst of a global pandemic. Starting a business — any business, not to mention the particular struggles of farm ownership — is a feat in itself, but Winterspring was doing so in an environment of uncertainty that was unprecedented in this generation, while also starting a family.
“There was a lot of doubt and uncertainty in the world. [We were] dealing with the pandemic, dealing with starting our young family and wondering if [we were] going to be here next year.”
Roxanne and Caleb were both experienced growers who were active in the local food community prior to starting their business. However, eventually, they found that in order to take their farm to a place of greater stability, they needed a solid marketing foundation that felt out of reach.
Taking stabs in the dark
“[As] first generation farmers, we are used to just figuring it out — tinkering around, taking stabs in the dark until you hit gold.”
As a writer and someone with some knowledge of digital communication, Roxanne had good instincts for DIYing Winterspring Farm’s marketing strategy. She knew how to create authentic content and was doing so regularly, but felt as though her message wasn’t quite landing. She realized that without a professional background in marketing, her approach felt scattered: she was spending a lot of time producing great content, but wasn’t sure if or how it was going to increase business or whether it was even being seen. On top of that, Roxanne and Caleb were spending “a ton of time and energy going through promoting positions, interviewing people, and feeling like [they] were in a position of desperation” when in came to staffing.
Striking Gold with Grapevine, VAPG, and Sustaining Farmers
“For all of my struggling in the dark, I didn't quite strike gold until we finally had Grapevine.”
If you’ve ever met Roxanne, you can tell she’s a problem solver. She noticed other farms in her circle that were doing a good job of marketing their businesses, and discovered that they were doing so through funding provided by a Value Added Producers Grant (VAPG). Because she saw how a unified marketing strategy helped her peers grow their businesses, she and Caleb applied for a VAPG with the help of grantwriter Sara Huber of Sustaining Farmers. Grapevine was able to provide a letter of support, and when Winterspring was awarded the grant, the team was able to hit the ground running.
“We wanted to replicate what we saw other farmers doing that worked. Once we got the grant, and started working with Grapevine, it was so easy. There are people that you can reach out to and hear back from. There are people who know you and you get to know them and wherever your [work] needs to go, it's going to get there.”
The first step of our partnership with Winterspring Farm was to develop a comprehensive marketing plan that focused on achieving their goals of:
Increasing CSA sign ups
Increasing seedling sale purchases
Increasing the size and value of individual orders
To achieve these goals, Grapevine implemented the following tactics:
An optimized Squarespace website as a companion to Winterspring’s Farmigo page, including the transfer of over 400 items including products and produce descriptions for the creation of a produce guide
Optimized the Farmigo page to make it more user-friendly and compatible with social advertising, leading to increased sales.
Developed a strategy for and implemented multiple targeted social media ad campaigns to encourage seedling sale purchases and CSA sign-ups
Developed email marketing and SMS text strategies that included templates and automations
Provided training, positioning the farm owners to implement these strategies successfully and with ease
Designed CSA boxes, custom magnets and a brochure that stand out to increase brand awareness
Results: Increasing sales & building community through effective marketing
“We had the biggest opening day of sales ever this year, and it just means so much.”
Two years later, Winterspring has had its best season opening ever. This is thanks to high-quality products, a community-minded business ethos, and a consistent outreach strategy that actively works to engage and retain new customers, resulting in a reliable base that continues to grow. In 2025, the farm credits the following results in part to their marketing efforts:
Biggest opening day
of their Seedling Sale
30% sales increase
year over year
Sold out CSA
2 years in a row
Seedling Sale
sold out
Improved mental health thanks to dependable sales
“[It] has alleviated a lot of anxiety that I didn’t even know I was carrying before because our sales are happening without so much work on our part. [We] can look back on the previous year's data and see a measurable growth. And that matters on a human level… to get a response back when you're working so hard to put something out into the world.
Fully and reliably staffed with less hiring effort
“We really haven't had to advertise any positions for hire for the last two years. So that is a major win. [It] has really helped us grow as a community, as a farm, and help us find crew members who are really dedicated to food and to ecosystem health.”
Ability to confidently plan for the future
“We suddenly stopped wondering if we're going to be here next year. And now we just have this feeling of yes, we're here. We got this. And we have the people and we have the power to continue.”
Improved SEO
+185% companion website visits during peak season
+155% Farmigo site visits during peak seasons
Optimized website
1000+ average monthly visitors to the companion website during peak season
70% of Farmigo store visits were referred from the optimized companion site
Social advertising
15% of new users came from social media, including presale advertising that has led to sold-out CSA and seedling sales
Strategic email marketing
13% of new website visits were acquired through an email marketing strategy that is highly targeted to lead to more sales.
Shout-out to the Winterspring Farm Family!
One of the things the Grapevine team loves about our work is the opportunity to lift up farms that have a positive social impact. Roxanne and Caleb have built a truly community-focused business, both in terms of their staff and their activism within the community. When speaking to us for this article, Roxanne called out each person on Winterspring’s staff and described how they came to the farm and what unique contributions they bring. Whether it was a sunny disposition and positive attitude, being the best transplanter around, or being a whiz at working with machinery, she had something specific and positive to say about everyone who works on the farm, including multiple first-year farmers and apprentices they are mentoring in order to support a growing young farmer cohort, which is vital to the future of our food supply.
Outside the farm, Winterspring is working to develop a cooperative farming model and is active in mutual aid projects in their area, donating produce to food pantries and other organizations working to relieve food insecurity.
Special thanks to Roxanne for the generous amount of time she took to speak with us for this article and for the contributions Winterspring and its staff make to supporting and strengthening the food system in Wisconsin.
