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Jon, CRO at Braintrust Tutors: Advize Career Interview
A music major's unexpected journey to Chief Revenue Officer at Braintrust Tutors reveals a dynamic career in educational technology.
The interview details a multifaceted role encompassing everything from cold calling and closing deals to high-level strategic planning and financial forecasting.
Success in this field requires a blend of sales acumen, data analysis, and a "teacher's mindset," with sales development representing an excellent entry-level opportunity.
The interviewee highlights the current booming EdTech market, emphasizing the rewards and challenges – particularly resourcing limitations in startups – while underscoring the importance of balancing business results with fostering positive work relationships.
A key lesson learned is the sometimes unsophisticated nature of some education companies regarding enterprise sales processes, a valuable insight for aspiring professionals.
This career path shows how academic excellence combined with strategic networking can lead to a rewarding and influential role at the intersection of education and business.
Advizer Information
Name
Job Title
Company
Undergrad
Grad Programs
Majors
Industries
Job Functions
Traits
Jon Small
CRO
Braintrust Tutors
McGill University 2000
MA NYU and MBA UCLA
Fine Arts, Music, Psychology
Education
Education
None Applicable
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Career Path Of A Chief Revenue Officer At Braintrust Tutors
Jon's career path took an unexpected turn from a music major to a successful career in education technology. After "dabbl[ing] in" internships and working part-time at Kaplan Test Prep, a large corporation in the early 2000s, Jon progressed from instructional roles to general management, eventually moving on to several education technology startups after six years.
Main Responsibilities of a Chief Revenue Officer at Braintrust Tutors
As Chief Revenue Officer at a startup, Jon's responsibilities are multifaceted, encompassing "everything from...cold calls to closing complex business cycles," reflecting the diverse demands of a growing organization. This includes both frontline sales efforts and high-level tasks such as "financial modeling and forecasting," showcasing the blend of practical and strategic roles common in Jon's startup experience.
A Day In The Life Of A Chief Revenue Officer At Braintrust Tutors
Jon's role as CRO at Braintrust Tutors offers "a ton of diversity," encompassing activities from "frontline sales" and investor meetings to financial projections and contract fulfillment. A typical day might involve a morning investor meeting followed by cold calling and then evening work on financial projections, showcasing the multifaceted nature of the position.
Most Important Skills for a Chief Revenue Officer at Braintrust Tutors
Jon, Braintrust Tutors' CRO, identifies two crucial skill sets: a deep understanding of "the sales process, building a sales team, and having a playbook for how to go to market," and a strong analytical ability to make "data-driven decisions" by interpreting daily, monthly, and annual data to inform company strategy. This blend of sales acumen and data-driven decision-making is essential for success in a revenue-generating role, particularly within a startup environment.
Favorite Parts of Being a Chief Revenue Officer at Braintrust Tutors
Jon, a seasoned professional with 15+ years of industry experience, appreciates the unique balance Braintrust Tutors offers: "the combination of being able to get on the phone myself and make sales calls...but then also be in strategic meetings." This blend of frontline work and executive-level strategy is not always available in larger corporations or startups, making it a particularly fulfilling aspect of Jon's current role.
Biggest Challenges Faced by a Chief Revenue Officer at Braintrust Tutors
Jon, Braintrust Tutors' CRO, identifies "resourcing" as the biggest challenge in their role, citing the company's small team and simple financial system. This means that even "great ideas" are often hampered by the need to carefully consider how each initiative impacts the company's "cash flow system" and overall financial health.
Favorite Parts of Working in the Education Technology Industry as a Chief Revenue Officer
Jon, Braintrust Tutors' CRO, finds the current period in educational technology to be a "Zenith of activity," comparing it favorably to the booming tech scene of the late 90s, and after nearly 15 years in the field, now finds the industry delivering "a lot of the rewards that had been pending for a long time."
What Type Of Person Thrives In The Education Technology Industry According To A Chief Revenue Officer At Braintrust Tutors
Jon, a CRO at Braintrust Tutors, highlights the key attributes for success in educational technology: a "teacher's mindset" combined with a strong understanding of sales and business. This resonates with their experience, echoing a former CEO's assertion that the core of Kaplan's success lay in "we teach and we sell," a principle that has guided their career.
What a Chief Revenue Officer at Braintrust Tutors Wishes They Had Known Before Entering the Education Technology Industry
Jon, a CRO in education technology, learned that some education companies are "a little bit unsophisticated" in their understanding of enterprise sales processes, legal paperwork, and revenue recognition. This lack of familiarity with core business functions creates "speed bumps," a fact Jon wishes he'd known beforehand to better prepare for navigating the industry.
Entry-Level Positions for Aspiring Sales Developers at Braintrust Tutors
Jon, a CRO at Braintrust Tutors, highlights sales development as an ideal entry-level position for undergraduates, stating that "you often don't have to have any sales experience at all," emphasizing the value of recent educational experience in selling education products. This role involves "Frontline prospecting," researching potential clients and passing qualified leads to senior sales staff.
Significant Career Lesson From A Chief Revenue Officer At Braintrust Tutors
Jon, a CRO at Braintrust Tutors, learned that balancing "the results you're trying to achieve in business" with fostering strong relationships and a positive work environment is crucial for long-term success. This involves considering how decisions impact "the various people who are around you," ensuring both productivity and happiness while achieving company goals.
College Experiences that Helped a Chief Revenue Officer at Braintrust Tutors Succeed
Jon's undergraduate experience involved initially prioritizing academic success ("getting good grades") before shifting focus to networking and building connections, recognizing their importance for post-graduation opportunities. This led Jon to advise students to concurrently pursue both academic excellence and relationship building, suggesting setting goals for each aspect to achieve a well-rounded undergraduate experience.
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