Manager, Distribution Readiness & Field Excellence - Openly

About Openly

Openly is redefining the insurance experience, replacing decades of complexity with clarity and modern technology. We’re the insurance provider people trust and the partner independent agents choose.

Job Summary

As Openly expands into new states and product lines, our distribution organization faces rising expectations from agency partners. The Manager of Distribution Readiness and Field Excellence serves as the coaching engine for our field sales team—driving performance not through one-off workshops or slide decks, but through deliberate, repeatable skill development. As a true player-coach, this individual deeply understands what great field execution looks like and builds the structured systems that empower reps to excel in every agent conversation.

Key Responsibilities

• Sales Skill Coaching: Lead 1:1 coaching, call reviews, ride-alongs, and group sessions targeting specific skill gaps in objection handling, consultative selling, and product positioning.
• Field Performance Framework: Define excellence for Openly sales reps by building dynamic competency models, assessment approaches, and feedback systems that guide ongoing rep growth.
• Learning Architecture: Design long-term learning pathways for rep onboarding, ongoing development, and market launches, partnering with Enablement to translate strategy into training content.
• Coaching Cadence & Accountability: Establish a repeatable coaching system across the team—including regular check-ins, rep development tracking, and structured feedback loops for field leadership.
• Agent Intelligence Integration: Ground coaching in real-time market data, using Voice of Agent feedback, competitive insights, and field observations to quickly adjust rep behaviors.
• New Hire Onboarding: Own the skill-development layer of new hire onboarding alongside Sales Enablement, ensuring reps are fully prepared for agent conversations from day one.
• Program Leadership: Manage and grow the coaching team over time, setting direction, maintaining high program quality, and connecting individual work to the broader coaching mission.
• Cross-Functional Partnership: Collaborate as a peer with Marketing, Product, and Distribution Leadership to help shape field launch strategy and execution ahead of new state or product releases.
• Agency Onboarding Content: Design the onboarding framework, content, and best practices that help new agency partners understand Openly and reach production faster.

Requirements

• 5+ years of experience in sales training, L&D, or field enablement, with a proven track record of directly improving field performance.
• Direct 1:1 coaching experience observing sales conversations, pinpointing skill gaps, and delivering actionable feedback that changes rep behavior.
• Industry or channel familiarity in insurance or B2B intermediary models (agents, brokers, advisors).
• Proven ability to build from scratch, including competency models and structured coaching programs.
• Practical skill development skills, with the ability to turn sales principles into concrete talk tracks, role-play scenarios, and tactical guides.
• High credibility and influence to build immediate trust with field reps and sales leadership.
• Clear, field-first communication style that delivers simple, immediately actionable resources rather than dense L&D documentation.
• People management capabilities to directly lead, hire, and scale a growing coaching team over time.
• Ability and willingness to travel 30–50%.

Preferred Qualifications

• Scaling experience building training infrastructure from the ground up in a fast-paced environment without slowing down active field ops.

Perks & Benefits

• Remote-first culture: Dedicated flexible work model supporting remote work.
• Competitive pay & equity: Base salary paired with equity ownership in Openly.
• Comprehensive health coverage: Medical, dental, and vision plans for you and your family.
• Life & disability insurance: Full coverage including voluntary supplemental options.
• Paid parental leave: Up to 8 weeks (320 hours) for eligible employees.
• 401(k) company contribution: 3% company gross income contribution regardless of personal contribution.
• Home office setup: $1,500 upfront workspace allowance plus a $75/month internet stipend.
• Professional development: $2,000 annual budget for courses, conferences, and resources.
• Wellness stipend: $50/month "Be Well" personal wellness stipend.
• PTO & volunteer hours: Paid time off to volunteer and referral bonuses.