VP, Product

Senior Product Executive

Second Nature is seeking a senior product executive to lead Product Management as a portfolio of businesses. This is the most senior product management role at the company, reporting to the Chief Product & Technology Officer with regular, direct exposure to the CEO/Founder and executive team given the strategic weight of the portfolio.

This role leads a team of Group Product Managers, each accountable for a product line as a business. Working with that group as general managers of their product lines to drive business outcomes is central to the job.

Why This Role Exists

Second Nature is converting strong bookings growth into long-term enterprise value by expanding the Resident Benefits Package category. This leader owns whether expansion happens, through a Product Management organization accountable for unit economics, revenue, and retention. The scoreboard:

• Attach rates across the core portfolio, with the mechanisms understood well enough to repeat as product lines expand
• The share of new revenue carried by newer product lines, broadening the portfolio beyond its current base
• Retention and new logo acquisition, with clear attribution to the work that drove them
• Unit economics across the portfolio, improved without trading away growth
• A roadmap that is a rationalized allocation of investment against business outcomes, resourced to execute and delivered against

The First 100 Days

• Discovery is funded as protected capacity, and prioritization is running on demand-side customer data
• Investment is focused on what customer evidence supports, and the organization understands the reasoning
• Group Product Managers are accountable for enrollment, revenue, and retention targets within their Product Domains
• The attach rate growth mechanism is defined for the core lines and being tested

How This Leader Operates

• Commercial Curiosity: Asks what moves revenue and what customers will pay for before asking what to build
• Disciplined Prioritization: Allocates investment against a stated methodology, and can explain what was displaced, what it cost, and why, whenever priorities change
• Talent Multiplier: Raises the bar on product talent and develops product managers into general managers of their lines
• Bias to Action Under Ambiguity: Moves decisions forward with imperfect information, and is energized rather than destabilized by speed and ambiguity
• Evidence Over Conviction: Changes direction when customer evidence contradicts the plan, including when the plan was theirs
• Cross-Functional Authority: Aligns GTM, Finance, Operations, and Engineering behind portfolio priorities using business logic those functions recognize, and carries Product Management's point of view on company-level questions that extend beyond its control
• Extreme Ownership: Owns the outcome, not the handoff - stays accountable when the result depends on work outside their control

Cross-Functional Partnerships

This role's success depends on four partnerships, each with a clear division of ownership:

• Engineering: Peer partnership on capacity, feasibility, and delivery. Product sets business outcomes and priorities; Engineering owns technical execution
• Finance and RevOps: Unit economics, line-level attribution, pricing, and portfolio margin
• Go-To-Market: Positioning, distribution strategy, new logo acquisition, and attach-rate mechanisms
• Customer Success and Operations: Retention drivers, post-sale experience, and the service constraints that shape adoption

Experience & Qualifications

• Has run multiple product lines simultaneously as distinct businesses, each with its own revenue, margin, and growth accountability, and has done so through a period of rapid growth rather than in a steady-state portfolio

• Has led a product organization of 20+ including a layer of product leaders, and has developed product managers into general managers rather than only hiring the capability in fully formed

• Has personally carried revenue and margin accountability for a product line, not delivery accountability alone

• Has operated inside a founder-led organization through a period of rapid growth and fast-changing direction

• Has partnered directly with GTM and Finance leadership on pricing, packaging, and commercial strategy

We get it. Requirements can sometimes hold people back from applying to a job, but don't let that be the case here. If you believe you have the skills it takes to elevate this role, team, and company, we encourage you to apply for this role.

Remote Work Statement

This is a remote-first, work-from-home position with required bi-annual in-person company meetings in January and July (business travel covered by Second Nature). You must be available during scheduled working hours, with a distraction-free work environment and reliable high-speed internet.

Why Second Nature?

Health First: Medical, Dental, Vision, & Life Insurance; 401K Plan

Location: Work Remotely from anywhere in the US

Flexibility: Open PTO and sick days

Culture: Diverse, inclusive, supportive, and growth-focused

Growth: Be part of a fast-growing team building a new category and making a real difference

The Product: Award-winning, customer-loved platform that truly delivers on our mission

Second Nature is an Equal Opportunity Employer and prohibits discrimination and harassment of any kind. We take action to ensure equal employment opportunities for all candidates and employees and to provide employees with a workplace free of discrimination and harassment. Our hiring decisions are based on business needs, job requirements and individual qualifications, without regard to race, color, religion or belief, family or parental status, or any other status protected by federal and/or state law.