The posting
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READY FOR YOUR NEXT CHAPTER?
Build the future of insurance with a team that values simplicity, empathy, and innovation.
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.
WHAT SETS US APART
- Technology that delivers: We use data to modernize underwriting and deliver tailored insurance solutions that fit how people actually live.
- Superior protection: Highly customizable coverage designed around what policyholders need.
- Effortless from quote to claim: Simple, intuitive workflows for independent agents and fast, human-centered care for policyholders.
OUR CORE VALUES
Our people are as important as our product. Collaboration, open communication, and work-life balance aren't just nice-to-haves, they’re at the core of how we operate.
We look for people driven by integrity, empathy, teamwork, curiosity, and urgency, because a great company starts with the right people.
DIVERSITY, EQUITY, & INCLUSION
We embrace individuality because everyone deserves to work somewhere they belong. We’re committed to building an inclusive culture that spans race, gender, age, religion, identity, and background.
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.
- Experience in the insurance industry (Personal or Commercial Lines) with a preferred understanding of B2B intermediary models (agents, brokers, advisors).
- Direct 1:1 coaching experience observing sales conversations, pinpointing skill gaps, and delivering actionable feedback that changes rep behavior.
- 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.
- 30-50% travel required.
Preferred Qualifications
- Scaling experience building training infrastructure from the ground up in a fast-paced environment without slowing down active field ops.
PERKS & BENEFITS
Great work happens when people feel supported. Our benefits are designed to care for you and your family at every stage of life.
- Remote-first culture: We supported remote work long before it became standard, and we remain dedicated to a flexible work model.
- Competitive pay & equity: Top-tier base salary paired with ownership in Openly’s growth.
- Comprehensive health coverage: Medical, dental, and vision plans tailored to you and your family.
- Life & disability insurance: Full coverage including voluntary supplemental options.
- Paid parental leave: Up to 8 weeks (320 hours) of paid parental leave for eligible employees (with additional disability coverage available for birthing parents).
- 401(k) company contribution: Openly contributes 3% of your gross income, regardless of whether you make personal contributions.
- Home office setup: A $1,500 upfront allowance to build your ideal remote workspace, plus a $75 / month internet stipend.
- Professional development: $2,000 annually to invest in courses, conferences, or resources to help you grow.
- "Be Well" program: A $50 / month stipend dedicated to your personal health and wellness.
- Volunteer hours & referral rewards: Paid time off to give back to your community, plus generous financial rewards for referring great talent.
Note: Select roles may also be eligible for cash incentives or sales commissions. Eligibility for all compensation and benefits is governed by applicable plan terms.
OUR HIRING COMMITMENT
Our process is designed to be transparent, respectful, and human. At every step, you’ll get to showcase your strengths, ask tough questions, and find out if Openly is the right fit.
U.S. Citizens, Green Card Holders, and those authorized to work in the U.S. for any employer and currently residing in the US will be considered.
Openly is committed to equal employment opportunity and non-discrimination for all employees and qualified applicants without regard to a person's race, color, sex, gender identity or expression, age, religion, national origin, ancestry, ethnicity, disability, veteran status, genetic information, sexual orientation, marital status, or any characteristic protected under applicable law. Openly is an E-Verify Employer in the United States. Openly will make reasonable accommodations for qualified individuals with known disabilities under applicable law.
We strive to provide an exceptional applicant and candidate journey when you engage with us. In an effort to respond to applicants in a timely manner, we leverage AI to organize applications and resumes based on required and applicable skills and experience. To allow our applicants to drive their initial interview experience with us, we may leverage an AI-supported scheduling tool so you can choose when to meet with our team. While AI assists with efficiency, all hiring decisions are made by our team members. Rest assured, your data is protected according to privacy laws and company policies. Contact our recruitment team with any questions about our AI-assisted hiring process.
