Director, Learning

About the role

The role Learning here serves two audiences: clients who need value from a product that changes every release, and our own team who needs to stay ahead of it. You'd lead the Learning team, own content and certification across both product lines, and sit in release planning alongside the Product and Marketing leads. The foundations are already good: a steady release cadence, our portals, a knowledge base, and a monthly scorecard the business actually reads. What's next is proving what all of that does for client adoption. It's a role with reach. Learning touches every client and every internal team, you'd have a seat where releases take shape, and you'd report to our COO. Where it goes from here is largely yours to shape.

Responsibilities

• Learning strategy, from internal onboarding through to client certification
• Manage the team: a learning experience designer, a technical writer, training consultants, and learning operations
• Participate in release planning as a peer to Product and Marketing, and oversee the content cycle that follows each release across the knowledge base, portals, and vignette library
• Own client‑specific learning environments alongside PractifiU, from build through retirement
• Manage the Learning budget and reporting that ties learning engagement to product adoption

Qualifications

• 5+ years of experience in learning, enablement, or technical training, with at least three years leading a team
• Proven track record running a documentation and LMS estate at scale and partnering with Product or Engineering on release‑driven content
• Habit of verifying product behavior yourself (e.g., opening an org and reading a permission set before writing)
• Experience in B2B SaaS, especially where rapid product changes made keeping content current a discipline
• Familiarity with Salesforce terminology is a plus
• Background in financial services or wealthtech is beneficial, or a strong aptitude for picking up specialist language quickly
• Experience using AI tools to build content and ability to describe how they changed your workflow

Pay

$130,000 to $145,000 base salary.

Benefits

• 20 days annual leave, 10 sick days, 3 personal days, and 3 volunteering days, all available from day one
• Learning stipend (“Learnbucks”)
• Two company summits per year in Chicago