Why should you be interested?

Rainier Recruiting is partnering with an early-stage fintech and AI startup transforming how local and regional retailers operate in one of the largest industries in the world. Our integrated platform combines modern point-of-sale, payment processing, and inventory management into a single system — giving small and midsized businesses the tools to compete with national chains. Our mission is to modernize independent retail operations, reduce waste, and strengthen local economies through smarter technology and data-driven insights. We’re looking for a new Customer Trainer. This is a high-impact, customer-facing role where you’ll work directly with business owners and store teams to activate new technology, improve processes, and help them run stronger, more efficient operations. You’ll be a core part of building the training function from scratch—crafting experiences that help users feel confident, supported, and successful.

If you enjoy teaching, traveling, problem-solving, and being hands-on with customers, this is an opportunity to make a meaningful difference at scale. Passive candidates who are employed and curious to hear are more than welcome to have a “no-commitment” conversation with our Recruiting team about why this could be an exciting career opportunity.

Compensation: $80,000 – $100,000 base salary (negotiable based on experience) plus bonus.

Work Model: Hybrid with extensive travel (4–5 days/week)

Location: Candidates based in the Bay Area, Southern California, New York Tri-State area, or near a major metro airport preferred

Openings: 2 roles, hiring immediately

Visa: Sponsorship not available

Why You’ll Love This Role

Join a fast-growing technology company that’s transforming how independent retailers operate, modernizing everything from inventory workflows to point-of-sale with intuitive, AI-driven tools.

This is a high-impact, customer-facing role where you’ll work directly with business owners and store teams to activate new technology, improve processes, and help them run stronger, more efficient operations. You’ll be a core part of building the training function from scratch—crafting experiences that help users feel confident, supported, and successful.

If you enjoy teaching, traveling, problem-solving, and being hands-on with customers, this is an opportunity to make a meaningful difference at scale.

What You’ll Do

• Lead engaging training sessions for new and existing customers, delivered both onsite and remotely
• Travel frequently to customer locations to facilitate go-lives, coach teams, and troubleshoot in real time
• Tailor your approach to audiences that range from tech-comfortable users to first-time digital adopters
• Build confidence and enthusiasm among users by answering questions with clarity, empathy, and patience
• Gather feedback from stores to help improve training content, onboarding processes, and product usability
• Contribute to the creation and refinement of training materials, including slide decks, scripts, and guides
• Partner closely with onboarding, customer success, and product teams to stay aligned on updates and user needs

Who You Are

• Energized by helping others succeed and skilled at delivering information clearly and effectively
• Comfortable in dynamic, fast-moving environments with changing priorities and tight timelines
• Excited to travel frequently and meet customers where they are—often onsite in store environments
• Known for your patience, positivity, and ability to adapt your communication style to diverse audiences

What You Bring

• 3–5 years in training, customer onboarding, implementation, education, or similar roles
• Experience delivering both in-person and virtual sessions
• Background in retail tech, restaurant tech, POS systems, or SaaS is highly valuable
• Experience working in a startup, entrepreneurial, or resource-constrained environment
• Strong facilitation and group management abilities
• Familiarity with CRMs and learning tools
• Ability to convert technical concepts into simple, actionable instruction
• Comfort using software tools and navigating multiple systems at once
• Willingness to travel up to 4–5 days per week
• Based in a major metro hub with easy access to airports

Who is Rainier Recruiting?

Rainier Recruiting is a boutique, award winning national staffing agency and executive search firm. Using an approach that “treats every candidate like an executive search”, we offer positions in contract-to-hire, Full-Time, and executive search. Named the #1 Best Workplace in Washington State in 2022, recognized as a ClearlyRated Best of Staffing firm, and identified as a top recruitment firm by multiple business journals, Rainier Recruiting is fast becoming a respected company. We are no longer the “best recruiters you have never heard of”. Rainier Recruiting is also proud to share our clients have a 93% repeat business rate. Rainier Recruiting is an equal opportunity employer and service provider and does not discriminate on the basis of race, religion, gender, gender identity, national origin, citizenship status, sexual orientation, disability, political affiliation or belief, or any other protected class. We are committed to the principles of Equal Opportunity Employment and are dedicated to making employment decisions based on merit and value, for ourselves, our client companies, and for the candidates we represent. We engage in socially conscious business practices and believe that diverse, equitable, inclusive, and non-biased talent and recruitment processes are foundational to the success of every organization that we partner with.