Chief of Staff, Sales Operations

About Us:

Clasp is a venture-backed, mission-driven startup transforming access to education and career pathways. We are revolutionizing the way employers attract and retain critical talent, while simultaneously tackling the student debt crisis. (Yep, we think BIG.) Our innovative platform meaningfully connects employers, educational institutions, and diverse talent to drive mutual benefit—using accessible education financing as the thread. We like to think of ourselves as more than a fintech; we’re a catalyst for economic mobility. 

A Forbes Fintech 50 company, portfolio company of SHRM (Society of Human Resource Management — the largest HR organization out there!), and recipient of “Startup of the Year” by StartUp Boston, Clasp is driven by our commitment to social impact and innovation. We are reshaping the future of the workforce one opportunity at a time. Join us on our journey to give power to learners and unlock fulfilling careers that drive positive change in their communities and beyond.

What We Need:

Clasp is seeking a highly organized, proactive, and driven Executive Sales Support Specialist to support our Founder / CEO through our founder-led sales approach. This person will be essential in optimizing outreach and ensuring a seamless sales process for both Clasp employees and external stakeholders. The ideal candidate will be scrappy, resourceful, and capable of working autonomously in a fast-paced environment. They will also have exceptional attention-to-detail, along with clear, polished, and professional written and verbal communication skills.

The ideal candidate will sit in Chicago, IL or Boston, MA but we are open to considering a strong remote candidate.

What You'll Do

• Support the Founder / CEO by managing and optimizing sales outreach efforts on her behalf. 
• Attend select sales calls with Founder / CEO and review call recordings to identify and coordinate next steps required by the Clasp team. 
• Maintain an efficient system for tracking and following up on sales leads
• Assist in the prospecting of new clients and prepare prospect-specific materials for meetings and presentations.
• Coordinate and schedule meetings, both virtual and in-person, ensuring all logistics are seamlessly arranged.
• Collaborate with other departments as needed to support the sales process.
• Provide administrative support, including managing correspondence and documentation.
• Track progress and provide reports on key sales metrics.
• Respond to client inquiries and coordinate communication on behalf of the Founder / CEO.
• Proactively identify opportunities to streamline sales processes for efficiency.

What You'll Need

• 4+ years of experience in a high-stakes client facing role.
• Strong organizational and time management skills with a keen eye for detail.
• Exceptional written and verbal communication skills.
• Ability to work autonomously and take initiative without constant supervision.
• Ability to listen attentively, learn quickly, and not make the same mistake twice.
• Familiarity with CRM tools and sales tracking systems would be a plus.
• Demonstrated ability to multitask and manage competing priorities effectively.
• A proactive, "scrappy" mindset with the ability to problem-solve creatively.
• Willingness to travel if necessary and flexibility to adjust schedules as needed.
• Experience coordinating complex travel and meeting arrangements.
• A high level of discretion and professionalism when handling sensitive information.

What We Give In Return

• Competitive cash and equity compensation 
• Health benefits (health, vision & dental), 401k
• Commuter benefits
• Flexible PTO policy
• Opportunities to grow and perform in a fast-paced environment alongside a stellar team

If you are a highly driven individual with a passion for technology + mission, and you thrive in a dynamic and fast-paced environment, we want to hear from you! Join us in revolutionizing the workforce solution industry and making a meaningful impact on businesses worldwide. Apply now to be a part of our growing team!

We are committed to creating a diverse and inclusive workplace where all employees feel valued, respected, and empowered to contribute their unique perspectives and talents. Clasp is an equal opportunity employer and prohibits discrimination and harassment of any kind. We embrace diversity and are dedicated to providing equal employment opportunities to all individuals regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law.