Customer Training and Enablement Manager

A Little About Inn-Flow

At Inn-Flow, we’re more than a hotel software company - we’re a team on a mission to transform how the hospitality industry operates. Built by hoteliers, for hoteliers, our all-in-one back-office platform brings together accounting, labor management, payroll, business intelligence, and more into one seamless experience. Our technology empowers hotel operators to work smarter, make better decisions, and focus on what matters most: delivering exceptional guest experiences.  Inn-Flow is experiencing strong growth and momentum, backed by the strategic investment from Mainsail Partners. As we scale, we’re expanding the leadership team, accelerating innovation, and deepening our impact across the hospitality industry, all while staying grounded in the real needs of operators. 

Our commitment to both customers outcomes and employee experience has earned industry recognition, including multiple top honors from the 2026 HotelTechAwards and recognition as a Top 10 Best Places to Work in Hotel Tech and Triangle Business Journal’s #2 Best Place to Work. 

At Inn-Flow, you’ll have the opportunity to do meaningful work, grow your career, and be part of a company that’s shaping the future of hospitality technology. 

About the role

Inn-Flow is hiring a Customer Training and Enablement Manager to establish and scale our customer training, education, and enablement function from the ground up. This role will be a critical leader within the CX organization and will play a key role in shaping Inn-Flow’s digital customer experience. 

This is a senior, player-coach role for a proven builder — someone who has designed and scaled customer training and enablement programs in a growing SaaS company and is excited to both lead and execute. You’ll be responsible for building the strategy, programs, technology foundation, and team that will take customer education at Inn-Flow to the next level. 

In this role, you will initially lead a small team of trainers transitioning from Implementation, while also rolling up your sleeves to deliver training, build content, and own the systems that power our enablement ecosystem. Over time, you’ll help grow this team and function as Inn-Flow continues to scale. 

This role will partner closely with Product, Engineering, Implementation, Customer Success, and Support to deliver a cohesive, scalable, and product-led enablement experience across the customer lifecycle — from onboarding through long-term adoption and expansion. 

This is a hybrid role based in the Raleigh, Durham, Chapel Hill area, with in-office collaboration in Raleigh on Tuesdays and Thursdays. 

What you'll do

Build and lead Inn-Flow’s Customer Training and Enablement function from the ground up Develop and execute a comprehensive enablement strategy that blends live training, digital learning, and in-app education Partner with Product to design and implement a product-led onboarding experience that accelerates customer time to value Lead the implementation and expansion of in-app education using Pendo to drive learning, adoption, and feature discovery Launch, own, and administer a Learning Management System (LMS), serving as the hands-on system owner while building scalable learning architecture Design and build role-based digital learning pathways for customers and internal users Create and deliver one-to-many training programs, including webinars, workshops, and scalable virtual sessions Build customer certification programs that support onboarding, product mastery, and long-term adoption — with an eye toward future internal and partner use Contribute to and evolve Knowledge Base content, while leading the segmentation between self-serve knowledge and formal product documentation Lead the rollout of a new product documentation platform and integrate documentation into a broader digital enablement strategy Partner closely with the Implementation team to train new customers during onboarding and support trainers transitioning from Implementation into dedicated training roles Hire, coach, and develop a team of customer trainers who excel at both customer-facing delivery and scalable content creation Serve as a customer-facing leader, delivering training and enablement directly as programs and teams are being built Drive cross-functional alignment and change management across Product, Engineering, and CX teams Define and track enablement metrics across onboarding outcomes, time to value, adoption, and expansion 

Qualifications

Multiple years of experience leading Customer Training, Enablement, or Education in a SaaS environment Proven experience building and scaling customer enablement programs from the ground up Experience operating as a player-coach, balancing hands-on delivery with team leadership Strong understanding of product-led onboarding, digital enablement, and in-app education strategies Hands-on experience owning and administering an LMS and digital learning platforms Strong customer-facing presence with experience delivering live and virtual training Experience partnering cross-functionally with Product, Engineering, and CX teams Comfort operating in fast-growing, evolving organizations with ambiguity and change Strong program management, communication, and change leadership skills 

What Makes You Stand Out

Experience implementing or scaling Pendo or similar in-app guidance tools Experience building certification programs for customers and internal teams Experience designing knowledge ecosystems that balance self-serve content and formal documentation Background partnering closely with Implementation teams during customer onboarding Data-driven mindset with experience measuring training impact across onboarding, adoption, and expansion A true builder mentality — energized by starting from scratch and creating systems that scale Senior-level leadership presence with the ability to influence across functions and levels 

Why You'll Love Working at Inn-Flow

We believe great work starts with taking great care of our people.  

At Inn-Flow, you’ll enjoy:  Benefits • Health, dental, and vision insurance • Short-Term Disability & Life Insurance • 401(k) with a generous employer match  Time Off & Flexibility • Flexible vacation and PTO • Paid holidays plus a floating holiday • Paid volunteer time • Hybrid work schedule with in-office collaboration on Tuesdays and Thursdays in our Raleigh office (remote Mondays, Wednesdays, and Fridays)  Work Environment & Culture • A beautiful, modern office in downtown Raleigh • Employer-paid monthly parking • Monthly team socials and regular celebrations • Quarterly all-hands meetings • A culture rooted in recognition, collaboration, and growth • Smart, kind, and genuinely fun people who care about their work - and each other 

 

Equal Opportunity Employer Inn-Flow is proud to be an Equal Opportunity Employer, upholding a work environment free from discrimination and harassment. We make our hiring decisions based on business needs, job requirements, and individual qualifications, without regard to race, color, religion, family status, or any other non-business consideration. We stand firmly against discrimination and harassment in any form.