From Grocery Bagger to Running an SE Team at Ramp

Curtis Breedenthal recounts his unlikely path into solutions engineering, starting as a grocery bagger while pursuing a kinesiology degree at community college and Cal State Monterey Bay. After having his first child unexpectedly, he abandoned his physical therapy aspirations and joined Bill.com as a chat support representative, working simultaneously with keyboard proficiency issues while managing chat SLAs. Over several years, he progressed through customer success roles, eventually volunteering to help establish Bill.com's Houston office during a company expansion. This decision, though uncertain, led to him working sunrise-to-sunset hours mentoring CS teams. When he observed colleagues transitioning to sales engineering roles, he initially dismissed sales as sleazy, but after understanding that SEs focus on product expertise with sales acumen, he invested six months in self-training outside working hours—watching SE call recordings, practicing demos during his hour-long commutes home, and sending monthly check-ins to the SE director. This consistent effort resulted in a seamless transition when an opening finally appeared. At Bill, Curtis learned the critical distinction between support and sales: support requires over-explaining every step, while sales engineering demands brevity and confidence. He also learned future-selling—communicating about roadmap items without claiming they're available today. After a year, Curtis realized he was being paid below market rate despite his contributions and made the jump to Vic for a significant raise and exposure to enterprise sales, moving beyond the repetitive "demo monkey" transactional work of mid-market. The enterprise environment taught him the importance of bespoke demo prep, researching prospect stakeholders' LinkedIn profiles, limiting talk time to three-minute segments maximum, and building genuine human connections—exemplified by his practice of taking photos with customer brand touchpoints to build authentic relationships. Curtis then joined Ramp, one of the fastest-growing fintech companies, where he progressed to become a Solutions Engineering Manager at the beginning of the year. His management approach emphasizes organizational best practices, sharing knowledge through documented workflows (Loom videos, structured onboarding), and tracking accomplishments beyond deal closes. The hosts highlight Curtis's exceptional documentation skills and his natural ability to help others without being asked. Throughout the discussion, Curtis and the hosts emphasize that the best demos are ones where you don't have to show anything—answering with conviction rather than visual proof. They critique AI-generated content that lacks human curation, particularly nine-page briefing documents that no one reads. The episode stresses that active listening is the most transferable skill from customer success to sales engineering, requiring genuine attentiveness, eye contact, and facial cues rather than multitasking. For aspiring SEs, Curtis emphasizes that work ethic beats talent, and breaking into the field doesn't require coding skills, Harvard degrees, or prior experience—only the willingness to talk to people, listen intently under pressure, and invest personal time to close knowledge gaps. The hosts recommend consistent follow-up and visibility (monthly check-ins, LinkedIn photos with target companies' products) to land opportunities.