VP, Product

Responsibilities

• Moves decisions forward with imperfect information, and is energized rather than destabilized by speed and ambiguity

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

This is a business leadership role first, expressed through outstanding product management. The right person is as fluent discussing customer lifetime value, unit economics, and market opportunity as they are discussing a roadmap or a discovery plan.

They read a business review the way an operator does - what is working, what is not, and what needs to change - and translate that read into clear direction for the leaders and teams who report to them. This leader treats product excellence as something measured by customer experience as well as business outcomes and holds the same standard across the portfolio.

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

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.