Enterprise Account Executive (Remote)

Enterprise Account Executive
Reports to: VP, Sales

About Us:

At BenchPrep, we are committed to revolutionizing learning by delivering the most advanced and flexible learning experience for certification, credentialing, test prep, continuing education, and training. Our learning platform helps associations, credentialing bodies and training companies deliver a highly engaging and effective learning experience for individuals looking to advance their careers. We incorporate the latest in learner-centered technology, including personalization, gamification, data science, usability and omni-channel delivery. The number of learners using our cloud-based learning platform has grown significantly, reaching nearly 12 million humans around the world in 2024, a testament to the success and impact of our innovative learning solutions.

Flexibility:

We’re committed to helping people learn better, and that starts with our own people. We are proud to be a remote-first company that empowers our team members to choose where they work best—whether from home, from our Chicago office, or a mix of both. We hire talent from across the United States, embracing the flexibility and inclusivity that remote work offers. Interviews and onboarding are conducted online, reflecting our remote-first culture. Our day-to-day work happens virtually, and so we are intentional to make time for connection and collaborations virtually as well.

While our remote-first culture is what works best for us, we also believe in the unique value of coming together in person from time to time. That’s why we host three “Together Weeks” each year at our Chicago office. During these events, we bring the entire team together for three days of learning, collaboration, and fun. These in-person gatherings are key to building strong relationships, sparking creativity, and celebrating our shared successes—while still preserving the flexibility of remote work for the rest of the year.

What you’ll do in the role:

We are looking for a highly motivated, self-starter sales executive to join our growing team. This Enterprise Account Executive (EAE) will be responsible for developing and closing new business within our Associations segment. Our most successful EAE’s are master relationship builders, internally and externally. They bring a natural curiosity to our product, our market, but most importantly, our prospect’s goals. That blend of relationship skills and curiosity is exercised through collaborative strategic solutioning of the BenchPrep product to our core market of associations and training companies. We don’t need our EAE’s to be technical experts; but they should know enough about the product to be dangerous while focusing energy on continuous discovery and relationships.

What you can expect:

New Logo Sales: This role is entirely new logo sales and not for those that want to manage accounts (in fact, after your deal is closed, it’s shipped off to the implementation and later the customer success team to manage). That’s why we crave “hunters” for this role.

• Associations & credentialing bodies Segment: In this role, you’ll specifically be focused on accounts in our associations & credentialing bodies segments. These customers will use BenchPrep to power their online study programs (similarly to customers of ours such as ACT, CompTia, GMAC and the HR Certification Institute).
• Prospecting: As mentioned above, you won’t be handed a book of business to manage once you start. Instead, you’ll be handed a target account list to go after. You will be assigned a BDR to help you prospect, but we expect you to do about 30% of your own prospecting (70% coming from BDRs or Marketing).

Enterprise Deals: This is enterprise, consultative sales and therefore not a transactional sale. Our sales cycle tends to take at least about 6+ months from start to close, given the complexity of the product solution and the need to collaborate with multiple internal and external stakeholders. While it’s not likely you’ll close a deal every month, we do love an ambitious seller!

• Strategic/Consultative Selling: Our prospects and customers look at us as advisors on their learning platforms. You’ll be expected to navigate an org chart like none other and find the various decision makers and change your selling approach accordingly.
• Virtual Selling: We, along with most of our clients, are working remote. Most of your selling will be via phone and video calls, with occasional travel to conferences and/or clients.

How you’ll become successful:

• Develop and execute an account based business development approach to the associations market.
• Master and demonstrate product knowledge; ongoing curiosity about the product and roadmap
• In coordination with internal sales enablement resources such as Marketing and BDRs, build and take ownership of a long term account penetration plan with self determined iterative milestones
• Effectively communicate the BenchPrep value proposition (primarily virtually) to drive and convert leads to opportunities
• Coordinate with the product team to deliver powerful product demonstrations while mitigating technical and integration hurdles
• Participate in qualitative research to understand the goals of the customers and customers of their customers; Work in coordination with Marketing on updating buyer personas

Skills & Experiences We Value:

• We tend to seek around 6+ years of direct sales experience in an Account Executive or equivalent quota carrying role.
• Proven experience and capability of carrying a quota and reaching (or exceeding) sales quotas of over $750K annually.
• Experience working with Enterprise level sales ($100K and above) in matrixed organizations where decision making is distributed and proven experience managing and closing complex sales-cycles and selling into Associations or similar organization types where Board approval is part of the buying process.
• Experience in Education Technology, specifically focused on the Associations segment strongly preferred for this hire.

At BenchPrep, we value our differences, and we encourage all to apply—especially those whose identities are traditionally underrepresented in tech. Research shows that candidates from underrepresented backgrounds often don’t apply for roles if they don’t meet all the criteria. We strongly encourage you to apply if you’re interested and even if you don’t meet 100% of the listed requirements. We’d be excited to see how you can boast our team with your unique experience.

Life at BenchPrep:

We work at BenchPrep because we’re dedicated to the mission and each day we have an opportunity to be challenged and learn. We work hard and have lots of fun. Culture is our lifeline at BenchPrep. We celebrate our people, both professionally and personally. We care about learning so much that we offer employees annual stipend dollars to develop their skills so they can continue to operate everyday with new skills. It’s no wonder we’ve been selected so often on various Best Places to Work lists!

Comp & Benefits:

This role offers flexibility in terms of experience and expertise. Throughout the interview process, we’ll evaluate your background to determine where you align within our compensation range. The salary range for this position is between $100,000 – $120,000+ variable commission plan, and is set based on Chicago market data. Please note this refers to the amount BenchPrep is willing to pay at the time of this posting.

• Medical insurance covering 80% of premiums for you and your dependents.
• Dental, Vision, Short & Long Term Disability, Life Insurance and other Voluntary benefits.
• 401(K) Safe Harbor Non-Elective 3% Contribution
• Flex PTO (our version of unlimited PTO), Wellness Days, Birthday PTO, Winter Break + a generous company holiday calendar
• Annual Learning Stipend of $1,200
• Parental Leave
• $500 towards workstation setup upon hire, and a monthly stipend for other expenses after that
• … and the list goes on!

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Please note, we are unable to accept applications from candidates outside of the US at this time.

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