About Us

Our Story

Devin Schain, a serial entrepreneur with extensive experience in higher-education start-ups, saw his own children and their friends struggling to find career success in their early professional years. He observed that college career centers were struggling to get students prepared for their first professional job search. And those who landed jobs out of college were often underemployed and unfulfilled. When they went to look for the next, better job, they found the job boards lacking and didn’t have a “go to place” for lifelong career support.

Recognizing this a problem begging for a solution, Devin founded Playbook. Playbook is dedicated to helping universities and colleges build lifelong engagement with alumni by making it easy to offer the services alumni want most – career services and professional development.  

Relying on his 30 years of entrepreneurship experience, Devin was able to quickly complete the company’s first acquisition of CareerShift. The CareerShift platform has become the company’s foundation for providing lifelong career services to students and alumni. With a base of over 300 universities and colleges, Student Playbook will continue to add solutions that engage alumni and drive lifelong career success.

We are committed not just to creating alumni engagement experiences, but also driving the utilization of those solutions. We partner with schools to directly market these services alumni, raise awareness, and ensure alumni are aware of their alma mater’s commitment to their lifelong success. 

Similar to one of his previous successful start-ups, On Campus Marketing (OCM), Devin knew that a university-endorsed model had the potential to expand career services for alumni.  At OCM, Devin built relationships with over 1,000 colleges and universities. These schools endorsed OCM, which sold bedding, care packages, and other dorm essentials to students.

With Student Playbook, Devin is applying a similar model. Alumni need a trusted resource for lifelong career support and professional development. Career centers and alumni associations can build lifelong engagement and loyalty by offering these services to alumni.

Our Mission

Alumni networks are an incredibly valuable asset for colleges and universities. The ability of schools to leverage that asset for university advancement is directly related to the lifelong engagement of alumni. Recent research has revealed that there is often a disconnect with what alumni want from their alma mater and what they receive.

Our mission is to help colleges and universities adopt a “give before you get” approach to lifelong alumni engagement. We make it easy for schools to not only provide the services alumni want, but also to promote utilization of these services.

It starts with providing what research study after research study has shown that alumni want the most from their alma mater – career services.

Our suite of solutions provides students and alumni with the lifelong career preparation, professional development, and job search services they need to launch and advance their careers.

Our Purpose

Student Playbook provides a continuum of support for lifelong career engagement and success.

Meet our Team

Devin Schain

Founder & CEO

Devin Schain is the Founder & CEO of Student Playbook, as well as eight other start-ups. As a serial entrepreneur with extensive experience in higher-education start-ups, Devin started and sold On Campus Marketing (OCM). OCM built an extensive network of university-endorsed partnerships to make shopping for college dorm essentials easier and more affordable. Devin also started and sold several other start-ups in the education space including Campus MD/Access Health Group, Campus Direct and Educational Direct. Devin graduated from the University of Pennsylvania. He is married with 3 awesome kids, and lives in the greater DC area.

Chad Massie

EVP, Strategy and Systems

Chad is a technology and business strategy leader with 20+ years of experience designing web and mobile product solutions to serve the needs of students, educators, and educational institutions around the world. At Student Playbook, Chad is responsible the product strategy, vision and roadmap. Prior to this, he served in a number of executive strategy and product roles in higher education, including VP of Product & Technology and Chief Strategy Officer at the Common Application. He also worked as the Director of Higher Education Partnerships at Hobsons, where he successfully expanded their partner network while integrating the current product portfolio with technology acquisitions. Chad earned a Master’s in the Management of Information Technology from the University of Virginia and a Bachelor’s in Psychology from Duke University.

Val Matta

Managing Director, CareerShift

Val Matta is an accomplished business development executive, who co-founded CareerShift in 2005 to help individuals bridge the gap between education and employment.  She successfully grew the company from a start-up to an established platform with over 300 university and college clients and over 152,000 student and alumni users. In her new role with Student Playbook, Val is responsible for introducing new alumni engagement solutions to the existing base of CareerShift schools and potential new schools. Val is a frequent speaker on career management, networking, and job hunting strategies.   She has a BA from Saint Francis University, an MBA from Cleveland State University, and lives in Florida with her loving family and community.


Adam Levy

Chief Financial Officer (fractional)

Adam is an experienced finance executive with deep knowledge of the financial, operational, and investment sides of emerging growth companies. In addition to serving as the fractional CFO of Student Playbook, Adam is the CFO of Talent Inc, providing financial oversight as the company rapidly expands their product offerings. He is responsible for establishing the frameworks, policies, and procedures to ensure stable, responsible growth. He also served as the CFO of Helix Education, a data-driven enrollment technology company in the higher education industry. Adam has an MBA from the Cornell Johnson Graduate School of Management and a BA from the University of Michigan. 

Craig Heldman


Craig has 25+ of leadership experience in the education technology market. In addition to being the Chief Revenue Officer at Student Playbook, he currently serves as a board member and advisor for emerging businesses in the space. Previously, Craig led three different higher-ed businesses as CEO, including VisionPoint Marketing, a leading provider of enrollment marketing and analytics solutions. Prior to VisionPoint, Craig completed a successful exit as the CEO of iModules, the market leading SaaS platform for colleges and universities to drive alumni engagement and fundraising. He also spent 22 years at Hobsons, including 9 as CEO, a provider of student success solutions to colleges and universities.  Craig has a Bachelor’s Degree in Finance and Marketing from Michigan State University.

Michelle Zlakowski

Chief Marketing Officer (fractional)

Michelle has 20+ years of marketing, business writing, sales support, and customer success experience. At Student Playbook, she is responsible for the company’s marketing strategy, messaging, and communications and to multiple audiences. Prior to Student Playbook, Michelle served on the executive team of a medical education company, where she developed relationships with education associations and promoted utilization of medical education in a B2B2C model similar to Student Playbook. Michelle has an MBA from the University of Michigan and a BA from Duke University.

Larry Moneta


Larry served as the Vice President for Student Affairs at Duke University until May 2019. He joined Duke in 2001 after nearly 10 years at the University of Pennsylvania, most recently as Associate Vice President for Campus Services. Larry holds adjunct faculty appointments at Duke in the Hart Leadership Program at the Sanford Institute of Public Policy and at the Graduate School of Education at the University of Pennsylvania where he teaches in the Higher Education Executive Doctorate Program. Larry has a Ed.D. from UMass Amherst and is a Fulbright Scholar. Larry is married with 2 grown kids and lives in Durham, NC.

Student Playbook

© 2023 Student Playbook. All rights reserved.

Hi!  We uses cookies to ensure you have the best experience on our website.  Please visit our privacy policy for more information.