Mainstay

• Join Mainstay as a Field Flex Agent (1099 Independent Contractor Agent) and take control of your earning potential while providing essential real estate field services. • As a contractor, you will complete specific field tasks on behalf of Mainstay customers, earning compensation based on the work performed. • This is an ideal opportunity for licensed real estate professionals looking for flexible field work, additional income, or a way to stay active in the industry without full-time commitments. • Mainstay’s Field Flex Agent Program allows you to leverage your expertise in real estate while maintaining full independence, choosing the tasks that best fit your schedule.

• Join Mainstay as a Field Flex Agent (1099 Independent Contractor Agent) and take control of your earning potential while providing essential real estate field services. • Complete specific field tasks on behalf of Mainstay customers, earning compensation based on the work performed. • Leverage your expertise in real estate while maintaining full independence, choosing the tasks that best fit your schedule.

• You'll own both sides of the transaction — acquisitions and dispositions — for some of the largest institutional buyers and sellers of single family homes in the country. • On the acquisition side, you'll work quickly to put together and present offers, then negotiate ruthlessly on behalf of our customers. • On the disposition side, you'll manage listings end-to-end: getting them active, fielding and negotiating offers, and keeping deals together from contract to close. • This is a high-volume role at a fast-moving Series A startup. Tools change. Processes change. Customers each have specific playbooks you'll be expected to know cold. • This is the kind of work AI doesn't do well — judgment calls, hard conversations, and the dozen small decisions that keep a deal together.

• Join Mainstay as a Field Flex Agent (1099 Independent Contractor Agent) and take control of your earning potential while providing essential real estate field services. • As a contractor, you will complete specific field tasks on behalf of Mainstay customers, earning compensation based on the work performed. • This is an ideal opportunity for licensed real estate professionals looking for flexible field work, additional income, or a way to stay active in the industry without full-time commitments. • Mainstay’s Field Flex Agent Program allows you to leverage your expertise in real estate while maintaining full independence, choosing the tasks that best fit your schedule.

• Join Mainstay as a Field Flex Agent (1099 Independent Contractor Agent) and take control of your earning potential while providing essential real estate field services. • As a contractor, you will complete specific field tasks on behalf of Mainstay customers, earning compensation based on the work performed. • This is an ideal opportunity for licensed real estate professionals looking for flexible field work, additional income, or a way to stay active in the industry without full-time commitments. • Mainstay’s Field Flex Agent Program allows you to leverage your expertise in real estate while maintaining full independence, choosing the tasks that best fit your schedule.

• Join Mainstay as a Flex Agent (1099 Independent Contractor Agent) and take control of your earning potential while providing essential real estate services. • Complete specific tasks on behalf of customers, earning compensation based on the work performed. • Leverage your expertise in real estate while maintaining full independence, choosing the tasks that best fit your schedule.

• Contribute to all phases of product development, from ideation and prototyping to implementation and iteration • Build and evolve both frontend product experiences and backend services that power them • Fine-tuning existing models and optimize their performance for Mainstay use cases • Design reliable, scalable backend services to support AI-powered features in production • Leverage AI to modernize and automate legacy workflows in the real estate industry • Evaluate and benchmark LLM performance across latency, cost, accuracy, and hallucination rates • Tune prompts, chain-of-thought logic, and implement retrieval strategies such as RAG and vector stores • Monitor performance, safety, and cost of LLM-driven features in production environments • Define and build useful LLM-powered experiences in partnership with cross-functional teams • Mentor and support the growth of other engineers on the team • Collaborate closely with product managers, designers, and operators to identify and solve customer pain points

• Lead the entire engineering organization (approximately 25 people) across all product engineering teams. • Define what an AI-first engineering org actually looks like at Mainstay. • Build an engineering culture where the bar is high, feedback is direct. • Make clear, timely decisions about team composition and performance. • Bring engineering a credible, trusted voice in product decisions. • Partner with the CPO and product managers on org design, hiring, and how engineering should evolve.

• Own prospecting through close for mid-market accounts ($10K–$100K+ ACV). Run discovery, product demos, and commercial negotiations across multiple product lines. • Land new customers through our seat-license platform, then cross-sell Tax, HOA, Data, Mail, and Revenue Management services to grow accounts into full-service relationships over 12-18 months. • Partner with senior leadership on complex or larger deals. You bring the account context and commercial strategy; they bring executive relationships. • Build and maintain a disciplined pipeline in HubSpot. Keep it accurate and current: no stale deals, no inflated stages, no fiction in the forecast. • Co-author the mid-market sales playbook. Messaging, sequencing, objection handling, pricing strategy. If it doesn’t exist yet, you build it.

Are you an entrepreneurial, intellectually curious, and energetic person? Are you excited about working on new and exciting problems and driving large scale social impact. Mainstay is looking for a VP of Finance who has a wide scope and requires an operator who enjoys partnering across the company; this is not a siloed finance role. Success in this role requires comfort operating as both an executive partner and the primary owner of core financial work. Your scope includes Finance, Accounting, People Ops/HR, and RevOps. Your team includes a Senior Accountant, People Ops Manager, Renewal Manager and part-time RevOps. Who We Are At Mainstay we deeply care about the outcomes of our partners. We're an extension of their teams who work to understand their goals, strategic priorities and plans, and align our efforts to meet their needs as a true partner. We use technology to scale the science of student success coaching through a communications platform that coaches students to and through college. We are a Public Benefit Corporation, with a commitment to helping more students access and achieve higher learning. We use human-centered, AI-enhanced coaching to proactively help learners find the answers they need, wherever they are, whenever they need it--and offer colleges a way to scale one-on-one support to their entire student body. What You’ll Do - Own end-to-end financial operations and compliance, including accounting, month-end close, financial reporting, internal controls, and audit readiness - Lead FP&A, including budgeting, forecasting, cross-functional planning - Develop financial models, KPIs, and dashboards that improve visibility and decision-making. - Lead revenue accounting for a SaaS recurring revenue business, including deferred revenue and revenue recognition - Manage cash, working capital, and liquidity planning, including forecasting and day-to-day cash oversight - Partner with the CEO and executive leadership on strategy, investment decisions, and resource allocation - Partner with PeopleOps Manager on all HR and PeopleOps items - Partner with Renewal Manager and RevOps on pricing and customer contracts What You’ll Have - 10+ years of finance leadership experience, spanning accounting and FP&A - High degree of operational rigor, with experience establishing disciplined forecasting, budgeting and KPI reporting - Ability to partner cross-functionally with Sales, Product, Operations & GTM leadership to drive data-backed decision-making and accountability; ability to translate financial insights into clear business actions - Excellent analytical and communication skills, with executive-level presence - Proven ability to scale finance operations in a growth-stage environment, building processes and infrastructure that support growth. - Highly organized and results-driven. Strong prioritization skills - Experience in early and/or growth stage startups is preferred Mainstay is committed to creating a company where all employees regardless of background can show up and feel they belong. We are proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or fitness level. The minimum pay for this role is $200K - $250K depending on the level you’re hired at. Actual compensation packages are based on a wide array of factors unique to each candidate including but not limited to demonstrated skill set, years & depth of experience, and some role dependent factors that can include certifications and software expertise. We also hope you’ll consider and be open to what else we provide outside of our base compensation. This includes our benefits, perks, equity, and other aspects of our overall employer brand including our culture which is built on our mission, vision and values. We welcome direct conversations with each candidate about compensation in all our initial calls.