MEET THE TEAM

The Succeeding Small Team

We are proud to introduce the passionate experts that make up the team at Succeeding Small. As a digital marketing agency based in Colorado Springs, we deploy strategies that are as unique as the entrepreneurs we’re serving. With diverse skill sets and backgrounds, our in-house team of specialists comes together with a shared passion for innovation, creativity, and giving back to the small business community. We are dedicated to continuous growth and improvement, where we always take pride in the work that we create.

MADELEINE COSTA

My name is Madeleine Costa, founder of Succeeding Small. I began my company when I realized I sought something different than the large-scale marketing companies that dominated the market. I wanted to serve the small businesses that reminded me of those that made up my family for generations. It was important to me to provide superior marketing at an affordable price.

After earning my Bachelor’s degree in English and Marketing, studying the complex algorithms that search engines use to rank websites and successfully managing dozens of digital marketing campaigns, I have been able to form a deep understanding of how to successfully grow small businesses online.

MAKAELA
POWILLEIT

As a Colorado Springs native, I love that my job allows me to give back to the small business community that helped shape my Colorado Springs experiences. Whether you’re a family chiropractor or a photographer, I always enjoy being able to experience an entrepreneur’s journey to becoming a successful small business owner.

My favorite part about being an account manager at Succeeding Small is forming genuine relationships with our clients. As the communications bridge between our clients and the Succeeding Small team, I’m able to tap into our clients’ needs and help our team craft meaningful communication strategies.

MADISON BOWERS

As the operations manager at Succeeding Small, I have the pleasure of helping our team stay organized and making sure our clients’ needs are always met in a timely manner. During my career, I’ve helped startups and small businesses in the nonprofit sector implement organizational systems and processes. If there’s an area of opportunity for a business to run more efficiently, I’ll find it!

The most rewarding part about working for Succeeding Small is seeing people live out their dreams of becoming small business owners. My entire life, I’ve been surrounded by a family of entrepreneurs, including my husband and myself. I’ve grown to have an authentic understanding and appreciation for all of the courage and work that goes into becoming a successful small business owner.

Maddy FitzHenry

I was first introduced to Succeeding Small as an intern while pursuing my business marketing and philosophy degree from UCCS. In the internship program, I fell in love with working with small businesses, seeing them grow, and getting them the digital visibility that they deserve.

I now work as a copywriter for Succeeding Small where I create unique content for local businesses to grow their online presence. It is incredibly rewarding to work with small businesses and their owners, hear their stories, and deliver engaging content to boost their brand awareness in today’s digital world.

JASON SWAIN

I started working in the affiliate space in 2017, looking to create commercial websites while living in Asia. I dedicated a significant amount of time in those years to studying SEO principles and found some success in getting small websites to rank. Every year I would head to Thailand for the annual SEO Conference to try and learn new strategies from thought leaders in the industry.

In 2019, I hosted the Shenzhen SEO Conference, introducing several notable figures from China and abroad involved in internet commerce. In 2021, I decided to approach what I’d learned professionally and apply the strategies to local SEO and joined Succeeding Small.

Sarah Cumens

I grew up in a small town in Pennsylvania that loves and supports all small businesses which is how I fell in love with helping small business owners. As a website designer, I get to help small business owners in an impactful way.

I’ve been designing websites for almost 3 years now and love to take a website that isn’t meeting the business’s goals and turn it into a converting website. I enjoy coming up with creative, innovative solutions to help small business owners succeed, which is exactly what I get to do at Succeeding Small.

Jenna vandebrake-page

I grew up in Colorado Springs and first fell in love with the small business community during college. During a gap semester, I took a job at a local bar, restaurant, and cinema. The staff and owners truly became like family, and I served and bartended there until I finished my M.A. Since then, I’ve worked at several small restaurants and bars in the Colorado Springs area while honing my copywriting skills with freelance blogging and web writing.

Succeeding Small allows me to combine my love for small businesses with my passion for writing. As a copywriter, I get to work on a variety of projects, from email marketing and social media to writing web pages. I love using psychology and my knowledge of human behavior to help small businesses succeed!

mallorie trichell

My professional background is in the medical field, where I was an Occupational Therapy Practitioner in the non-profit sector. That role led to a management position that encompassed marketing, and I have been fascinated ever since.

I now enjoy creating social media strategies and content for small businesses, allowing me to express my creativity.

One-of-a-Kind Digital Marketing Internship

In addition to our incredible team, we are also proud to offer a digital marketing internship program. We prioritize education and continuous learning, and this program allows us to extend that culture into the student community. We partner with UCCS and other universities in Colorado Springs to educate students in digital marketing. During the internship, students learn every service we provide, work with real small businesses, and get the opportunity to find what they’re most passionate about within the world of digital marketing.

Want to Work with Us?

Are you looking for a career in digital marketing? Learn more about our culture and what it is like to work at Succeeding Small! Whether you are a student, marketer, or community member ready to be a part of a full-service digital marketing agency, we’d love to meet you. Check out our marketing job opportunities or our internship program today.

MEET THE TEAM

The Succeeding Small Team

MADELEINE COSTA

MAKAELA
POWILLEIT

MADISON BOWERS

Maddy FitzHenry

JASON SWAIN

Sarah Cumens

Jenna vandebrake-page

mallorie trichell

One-of-a-Kind Digital Marketing Internship

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