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Second Nature

Subscription-based resident benefits for property managers

Vice President Product

Full-Time
No salary listed
Expert
Remote in USA
RemoteRemote within the US, with required bi-annual in-person company meetings in January and July.
ProductProduct Management

About the job

Requirements
  • Has run multiple product lines simultaneously as distinct businesses, each with its own revenue, margin, and growth accountability, through a period of rapid growth.
  • Has led a product organization of 20 or more, including a layer of product leaders, and has developed product managers into general managers.
  • 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 go-to-market and Finance leadership on pricing, packaging, and commercial strategy.
  • Must be available during scheduled working hours, with a distraction-free work environment and reliable high-speed internet.
Responsibilities
  • Lead Product Management as a portfolio of businesses.
  • Lead a team of Group Product Managers, each accountable for a product line as a business.
  • Own expansion of the Resident Benefits Package category through a Product Management organization accountable for unit economics, revenue, and retention.
  • Drive attach rates across the core portfolio and define mechanisms that can be repeated as product lines expand.
  • Increase the share of new revenue carried by newer product lines.
  • Own retention and new logo acquisition with clear attribution to the work that drove them.
  • Improve unit economics across the portfolio without trading away growth.
  • Create a rationalized roadmap that allocates investment against business outcomes, is resourced to execute, and is delivered against.
  • Fund discovery as protected capacity and run prioritization on demand-side customer data.
  • Focus investment on customer-supported opportunities and communicate the reasoning to the organization.
  • Hold Group Product Managers accountable for enrollment, revenue, and retention targets within their product domains.
  • Define and test the attach-rate growth mechanism for the core product lines.
  • Allocate investment against a stated prioritization methodology and explain displaced work, cost, and rationale when priorities change.
  • Raise the bar on product talent and develop product managers into general managers of their product lines.
  • Move decisions forward under ambiguity and changing information.
  • Change direction when customer evidence contradicts the plan.
  • Align go-to-market, Finance, Operations, and Engineering behind portfolio priorities using business logic.
  • Represent Product Management's point of view on company-level questions extending beyond its direct control.
  • Own outcomes rather than handoffs and remain accountable when results depend on work outside Product Management.
  • Partner with Engineering on capacity, feasibility, and delivery while Product sets business outcomes and priorities.
  • Partner with Finance and Revenue Operations on unit economics, line-level attribution, pricing, and portfolio margin.
  • Partner with Go-to-Market on positioning, distribution strategy, new logo acquisition, and attach-rate mechanisms.
  • Partner with Customer Success and Operations on retention drivers, post-sale experience, and service constraints shaping adoption.
  • Attend required in-person company meetings in January and July.

About the company

Second Nature provides a resident benefits package for property managers through a per-resident, monthly subscription. The package includes services such as filter delivery, rent rewards, and credit reporting, all designed to help property managers attract and retain tenants. How it works: property managers pay a fixed monthly fee for each resident, and the benefits are delivered to residents as part of the package, enabling managers to streamline operations and potentially improve their bottom line. How it differs from competitors: it offers an integrated, recurring-revenue bundle of tenant-focused services tailored specifically to property managers, combining amenities (like filter delivery) with financial perks (rent rewards and credit reporting) in a single subscription. The goal: provide a predictable, scalable revenue model for property managers while improving tenant retention and property performance.

Company Size

201-500

Company Stage

Series C

Total Funding

$35.9M

Headquarters

Raleigh, North Carolina

Founded

2012

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Simplify Jobs

Simplify's Take

What believers are saying

  • Second Nature updated its RBP pages in July 2026, showing active product investment.
  • Its resident benefits package targets single-family portfolios, a large recurring-fee market.
  • The October 2025 $22 million Series B funds expansion and product refinement.

What critics are saying

  • Beagle advertises Renters Kit at $4 per unit, crushing pricing power.
  • Resident benefit fees face disclosure and tenant-backlash pressure as lease add-ons.
  • The AI roleplay and resident-benefits narratives signal strategic drift that can confuse buyers.

What makes Second Nature unique

  • Second Nature bundles eight resident perks into one fully managed package.
  • Maestro personalizes onboarding and benefits by property type, location, and resident profile.
  • Automatic enrollment and 24/7 support reduce property-manager workload versus fragmented point solutions.

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Benefits

  • Health Insurance
  • Dental Insurance
  • Vision Insurance
  • Life Insurance
  • 401(k) Retirement Plan
  • Unlimited Paid Time Off
  • Remote Work Options
  • Professional Development Budget

Growth & Insights and Company News

Headcount

6 month growth

1%

1 year growth

1%

2 year growth

3%
Financial 247
Oct 30th, 2025
Second Nature Secures $22M Series B

Second Nature, an AI roleplay platform, has raised $22 million in a Series B funding round led by Sienna VC, with participation from Bright Pixel, StageOne Ventures, Cardumen, Signals VC, and Zoom. The funding will be used to expand operations and enhance its AI sales training technology. Second Nature's platform, used by major brands like Oracle and Zoom, improves sales performance and reduces onboarding time. The company aims to integrate AI training into team workflows.

ExploreBit
Jan 12th, 2022
Venture Capital Bank invested into Secondnature in $12.5M on Jan 12th 22'.

Second Nature, the automated AI-powered sales coaching solution, today announced the company's launch alongside a $12.5M Series A round of investment by signals Venture Capital, StageOne Ventures, Cardumen Capital, and Zoom Video Communications, Inc. via the Zoom Apps Fund.

PR Newswire
Jan 12th, 2022
Secondnature recognized as 2021 Gartner® Cool Vendor in Conversation Intelligence on Dec 12th 21'.

Second Nature was recently named a 2021 Gartner® Cool Vendor in Conversation Intelligence.