Openly is rebuilding insurance from the ground up. We are re-envisioning and enhancing every aspect of the customer experience. Doing this requires a rapidly growing team of exceptional, curious, empathetic people with a wide range of skill sets, spanning technology, data science, product, marketing, sales, service, claims handling, finance, etc.
The Openly DifferenceWe created Openly because we saw an evident gap in the market for premium insurance made simple. Consumers deserve more complete coverage at competitive prices.
- The Price Difference: Using cutting-edge data and technology, we provide you with customizable, competitive prices to protect your most valuable assets.
- The Policy Difference: Coverages are truly customizable to meet your individual protection needs, for both standard coverages and optional add-ons.
- The Experience Difference: From tailored claims handling to highly responsive customer service, we are focused on making the home insurance purchasing process a better overall experience.
At Openly, our people are just as important as our product. For us, collaboration, communication, and work-life balance are more than nice-to-haves— they’re the must-haves that make us who we are. We believe a great company is the result of a shared set of values, so we look for these qualities in every candidate we hire.
- Integrity
- Empathy
- Teamwork
- Curiosity
- Urgency
We've designed our hiring process with you, the candidate, in mind. At every step, you have the chance to present your strengths and learn more about what makes Openly a great place to work.
We're committed to Diversity, Equity, & InclusionWe embrace individuality and believe diverse teams are winning teams. Our commitment to inclusion across race, gender, age, religion, identity, and experience drives us forward every day.
Job Details
As the Director of People Strategy and Enablement, you'll be a pivotal senior leader on our People & Culture team. Reporting directly to the VP of People and Culture, you will be the architect of a thriving, high-performance remote work environment. You will lead and mentor a talented team across People Solutions, Organizational Effectiveness, and Communications, shaping the strategies that empower our leaders, engage our employees, and drive our business objectives forward.
This isn't just a role about running People programs; it's about building the operating system for our company's culture and growth.
How You'll Make an Impact- Shape Our Narrative: You will design and execute a multi-channel internal communications strategy that ensures every employee feels connected, informed, and aligned with our company's mission and priorities. You'll leverage modern tools, including AI, to create compelling content and measure its effectiveness.
- Build High-Performing Teams: You will act as a trusted advisor to our leadership team, helping them build more effective and cohesive units. You'll implement our leadership model and use data from engagement surveys and 360s to drive meaningful change and organizational health.
- Drive Strategic People Solutions: You will lead our HR Business Partners to translate business goals into actionable people strategies. This includes everything from strategic workforce planning and building career paths to managing employee relations and evolving our performance management frameworks.
- Champion a Thriving Remote Culture: You will spearhead key employee experience programs, including DEI initiatives and coaching, to foster a collaborative and inclusive remote-first environment.
- Extensive HR Leadership Experience: You have 7-10 years of progressive experience across organizational effectiveness, HR business partnering, and talent management, preferably within a fast-paced tech or insurtech company.
- Strategic Vision: You possess a demonstrated history of developing and implementing talent strategies from inception, effectively addressing and foreseeing the evolving needs of a growing organization.
- Masterful Stakeholder Management: You excel at building trust and influencing outcomes with partners at all levels, from individual contributors to the executive team. You are an experienced and empathetic people manager.
- A Data-Driven Mindset: You are skilled in using quantitative and qualitative data to identify trends, measure success, and tell a compelling story that drives action.
- Change Management Expertise: You have successfully led organizations through significant change, creating the playbooks, communication plans, and buy-in needed to ensure smooth transitions.
People Solutions
Drive a high-performance culture through a tailored approach to organizational design, superior employee and leadership support, and talent development at all levels.
- Lead strategic business partners to align people strategy with business objectives
- Strategic workforce planning, capability modeling
- AI-enabled career pathing/job architecture
- Functional bench strength planning and training
- Technology-enabled learning and development
- AI-enabled policy, compliance, and employment regulation ownership
- Employee relations
- Performance management, succession planning, and talent frameworks
- Employee experience programs including DEI, coaching, and microcultures to support an effective, collaborative remote environment
Organizational Effectiveness
Accelerate functional/cross-functional effectiveness and buy-in for major change initiatives.
- Leadership operating systems
- Leadership frameworks
- Execution of the Openly Leadership Model
- Culture assessments, engagement surveys, 360s, etc
- Change management playbooks, communication across major initiatives
- Implementation and communication plans with clarity in ownership, accountability, decision-making, and expectations
Communication & Enablement
Create and execute a strategy that supports alignment and focus through effective communication across the company.
- Strategic communication enablement
- Content strategy for company-wide messaging, information cascade, multi-pronged communication framework
- AI-enabled content, workflows, and success insights
- 7-10 years of progressive experience in organizational effectiveness, business partnering, and talent management in a dynamic business environment
- Exceptional team, partner and stakeholder management skills
- Experience evolving a talent management strategy to support strategic company objectives
- Proven success with change management initiatives and playbooks
- Quantitative skills to enable a data-driven approach to People and Culture success
- Demonstrated ability to effectively communicate insights to leadership and stakeholders
- Proficiency in traditional and creative development approaches to support diverse business functions
- Excellent written and verbal communication skills
- Exceptional project management skills
- Experience in a technology company is strongly preferred
Compensation & Benefits:
The target salary range represents the budgeted salary range for this position. Actual compensation for this position will be determined based on the successful candidate's experience and skills. We are committed to providing a compensation package that not only reflects the responsibilities and requirements of the role, but also the unique expertise that the chosen candidate will bring to our team.
The full salary range shows the min to max salary range for this position. Actual compensation will be commensurate with experience and qualifications and determined based on various factors including the candidate's qualifications, skills, and experience.
Benefits & Perks
- Remote-First Culture - We supported #remotelife long before it was a given. We'll keep promoting it.
- Competitive Salary & Equity
- Comprehensive Medical, Dental, and Vision Plan Offerings
- Life and disability coverage including voluntary options
- Parental Leave - up to 8 weeks (320 hours) of paid parental leave based on meeting eligibility requirements
(Birthing parents may be eligible for additional leave through STD) - 401K Company Contribution - Openly contributes 3% of the employee's gross income, even if the employee does not contribute.
- Work-from-home stipend - We provide a $1,500 allowance to spend on setting up your home workplace
- Annual Professional Development Fund: Each employee has $2,000 in professional development (PD) funds to spend on activities or resources annually. We want each Openly employee to achieve personal and professional success and to feel supported, confident, and informed about improving their efficiency and productivity.
- Be Well Program - Employees receive $50 per month to use towards your overall well-being
- Paid Volunteer Service Hours
- Referral Program and Reward
Depending on position, Employees generally are eligible for cash incentive compensation, including commissions for sales eligible roles. In all cases, eligibility for compensation and benefits is subject to applicable plan and policy terms in effect from time to time.
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.
Top Skills
Openly Boston, Massachusetts, USA Office
131 Dartmouth St, Boston, MA, United States, 02116
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