Our Leadership Team

Mike O'Brien
Senior Vice President, Sales

Josh Braunstein

“Innovation is about solving problems no one knew existed.” As President of OnCourse Learning, Josh has extensive experience in growing B2B and B2C businesses within the software, information/publishing, EdTech and professional service fields. Josh joined OnCourse Learning in February 2020. He is an expert in accelerating revenue and customer wins, leading successful acquisitions and championing user-focused design methodologies to drive innovation. Skilled at building a culture across geographies, Josh creates shared goals that fuel positive change and growth. Most recently as Executive Vice President at Worldstrides, the largest educational travel company in the US, Josh led global teams on six continents serving students in higher education with transformative experiences focused on study abroad, internships and service learning. Prior to joining Worldstrides, Josh was an Executive Vice President at Wolters Kluwer Tax and Accounting, a provider of B2B software, learning and workflow solutions. After successive leadership roles in operations and product management at Corsearch, a premier provider of intellectual property services and software, Josh assumed leadership of the business where he tripled revenue and quadrupled EBITA while transforming offerings and market position and expanding operations to six countries. Josh holds a BA in Political Science and East Asian Studies from Middlebury College in Vermont. He also studied International Relations at the London School of Economics.

Fun Facts About Josh

My three daughters are respectively a gymnast and lacrosse player, a hockey player, and an artist. I am good at none of those things.
As a family, we are avid skiers and hikers.
My hobbies include reef-keeping (we have multiple tanks) and wine collecting (we have multiple bottles).
While you can’t tell from my accent, both sides of my family come from Brooklyn, NY.

Todd Premo

“Creating effective products based in smart technology solutions and in response to real-world challenges has been a passion my entire career.” As the Chief Product Officer, Todd leads an organization of passionate individuals in the delivery of innovative product and technology solutions. With a focus on experience and delivering superior outcomes, our success is measured in the eyes of our users. Todd has over 23 years of product, technology, and leadership experience building high performing teams and market leading product solutions in learning and talent, healthcare, and environmental industries. Prior to joining OnCourse Learning, Todd led teams at Pulse, Inc. – serving the ambulatory healthcare market with clinical and practice management solutions. Previously, he focused on Talent and Learning solutions at Click2Learn, SumTotal Systems, GeoLearning, and Skillsoft where he helped introduce integrated talent systems and innovative offerings in virtual and mobile learning. Todd earned both BS and MS degrees in Engineering from Purdue University, has completed the Harvard Leadership program and is a Pragmatic Marketing alumnus.

Fun Facts About Todd

A self-proclaimed audiophile, I enjoy more than just listening. I have designed and built systems and entered competitions.
My frustration with fitness is clearly due to my wife’s awesome cooking.
Staying active with my kid’s activities has turned into trying to keep up (see above).
Born in NY, lived in Japan, love to travel, and as a life-long boater, I especially love being on the water.

Ann Reist

“Marketing and sales alignment is key to achieving our market and revenue goals. To be successful we must provide the right messaging, to the right person, at the right time and we must demonstrate how marketing impacts the bottom line.” Ann leads the B2C and B2B go-to-market strategy at OnCourse Learning. Her team drives marketing strategy and execution by using data-driven insights to ensure a consistent stream of measurable inbound and outbound initiatives that increase awareness, drive conversions, pipeline and revenue, and positions OnCourse Learning as a leader in technology-based learning. Ann came to OnCourse Learning in April of 2017 and brings over 25 years in marketing strategy and execution. She has held marketing leadership roles in enterprise software and embedded technologies, education, healthcare, real estate, and direct marketing industries. She most recently led product marketing and demand generation for Flexera. Prior to Flexera, Ann held marketing roles at Follett Software Company, Enterprise Systems (purchased by McKesson), Melson Technologies, and LPC (purchased by Pitney Bowes). Ann has a Bachelor of Business in Marketing degree from Western Illinois University.

Fun Facts About Ann

I LOVE exploring the world. Learning about and exploring new places and cultures, puts me in my happy place.
I have an amazing (and very large) immediate and extended family that I love spending time with and sharing memories with.
I get excited reimagining old things – give me a hammer and a paintbrush and watch the magic!

Mike O'Brien

“Deliver high quality solutions & service where the value is so easily recognized it never needs to be pointed out.” Mike leads Sales and Client Experience functions within OnCourse Learning. He joined OnCourse Learning in June 2019 and has over 20 years of sales and marketing experience with a history of building and managing direct and channel sales organizations in Education, Healthcare and Postal Automation software industries. Mike is a Graduate of Northern Illinois University with BS in Business Administration and a Graduate of University of Phoenix with MBA. He currently live in Williams Bay, WI with Wife, Daughter, Son and our Beagle / Basset hound.

Fun Facts About Mike

I enjoy hiking, boating and apologizing to other golfers for being in their fairway
I’m a huge fan of classic cars and aspiring to get in the game someday soon
I have broken both wrists, both knees and a collarbone all while playing sports – all different accidents
Most memorable days: Wedding Day, Kids birth days and the Chicago Cubs finally winning the World Series

Kyle Bennett

“Passion is contagious. Leading through doing, rather than telling is the most effective way to create a passionate team.” Kyle Bennett leads OnCourse Learning’s webinar division previously known as Total Training Solutions (TTS). TTS was a 2018 acquisition that allowed OnCourse Learning to increase it’s market reach by offering leading webinars serving the training needs of the bank, credit union and mortgage industries. Kyle earned a BA in Economics from the University of Wisconsin-Madison. He then went on to earn his MBA from DePaul University. His career in the financial industry started as a Management Trainee with First American Bank in Illinois. Kyle then joined TTS in 2006 and his role has expanded from “Email Marketer” to Senior Vice President. Kyle currently resides in Mt. Prospect, Illinois with his wife and two daughters.

Fun Facts About Kyle

Our family cabin in northern Wisconsin is my favorite place on Earth…even in the winter when it’s under three feet of snow.
Snowmobiling is my favorite recreational sport. Yes, I’m one of those weirdo’s that love winter (see above).
I’m a proud owner of the Green Bay Packers. Go Pack GO!
Living with four women (wife, two daughters and our dog) has taught me a lot of things, but I still can’t braid my daughter’s hair.