• Lead the Final Expense Sales organization, responsible for managing multiple teams and driving performance • Define and own KPIs across production, activity, efficiency, and quality; foster a data-driven performance culture with clear accountability at every level • Lead, develop, and scale a high-performing team of licensed agents and managers — hiring top talent, building career paths, and maintaining a culture of performance • Build and continuously improve sales playbooks, scripts, and sales motions tailored to the Final Expense customer • Develop coaching programs across call reviews, shadowing, certifications, and performance improvement plans for both managers and agents • Partner with Product and Marketing teams to develop shared test and experimentation roadmaps • Set and manage staffing plans in partnership with Finance and Marketing, ensuring coverage, ramp capacity, and productivity targets are met • Design and evolve compensation plans that align agent and manager incentives with business outcomes

• Responsible for driving sales, developing business, and addressing customer needs within an assigned long-term care (LTC) territory. • Manages relationships with prescribers, pharmacists, facility decision-makers, and other members of the LTC care team to ensure appropriate patients are identified, started, and maintained on therapy. • Build and maintain strong relationships with all members of the LTC resident care team, including physicians, physician-extenders (NP/PA), consultant pharmacists, dispensing pharmacists, and nursing facility leadership/staff. • Promote Acadia products by delivering compliant clinical, disease state, and reimbursement education tailored to customer needs. • Identify and address customer questions, concerns, and objections with advanced selling skills. • Develop deep knowledge of customers, practices, and local/regional market trends; apply this insight to business planning. • Create and execute quarterly territory business/action plans, leveraging data to maximize reach, frequency, and impact within budget. • Provide guidance on pricing, reimbursement, and LTC-specific profitability parameters; act as liaison between customers and Acadia for access-related questions. • Collaborate with sales management, territory teammates, and cross-functional partners (e.g., managed markets, marketing, operations, training) to address business needs. • Represent Acadia at conferences, exhibits, product launches, and training sessions; contribute to regional and national initiatives. • Mentor and train new/junior Sales Specialists; share field insights and participate in cross-functional projects. • Maintain compliance with all regulatory requirements, company policies, and LTC regulations affecting medication use and resident care.

Role Description We’re looking for a Founding Head of Enterprise Sales to own sales execution across strategic accounts, with a particular focus on Fortune 1000 brands, large enterprise design teams, procurement-led buying processes, and AI training data opportunities. This is a high-ownership role for someone who can operate as a solo sales representative while also helping build the sales process, playbooks, reporting, and feedback loops needed to scale. You will: - Manage inbound demand - Develop targeted outbound opportunities - Run discovery and negotiation - Close new business - Forecast pipeline - Build a repeatable process for expanding client relationships and bookings over time You will be supported by SDR contractors who help field and qualify inbound requests, but you will own the full sales cycle for qualified enterprise opportunities. Qualifications - 4–7+ years of B2B sales experience, ideally in SaaS, marketplaces, enterprise software, data licensing, creative technology, design tools, media, or digital assets - Experience selling to large organizations, with Fortune 1000, enterprise, or procurement-led sales experience strongly preferred - Proven ability to manage full-cycle sales, including prospecting, discovery, stakeholder management, proposal development, negotiation, closing, and forecasting - Experience selling to or working with procurement, design managers, creative operations teams, marketing teams, legal stakeholders, or enterprise brand teams - Strong comfort with ambiguous or emerging deal types, especially where sales process, packaging, pricing, and internal workflows are still being built - Excellent written and verbal communication skills - Strong commercial judgment and ability to prioritize the highest-value opportunities - CRM discipline and ability to maintain clean pipeline data and reliable forecasts - Ability to translate customer conversations into actionable feedback for product, engineering, legal, and leadership - An approach that is self-directed, resilient, organized, and comfortable operating as the primary sales owner Requirements - Experience with AI training data, data licensing, content licensing, rights management, or enterprise licensing deals - Experience selling into design, creative, brand, marketing, or procurement teams - Experience working with marketplaces, creator platforms, design platforms, stock content, fonts, templates, or creative asset businesses - Familiarity with complex commercial conversations involving usage rights, licensing terms, legal review, compliance, or technical evaluation - Experience building sales processes, outbound campaigns, enterprise account plans, or expansion playbooks from scratch - Experience working with SDRs, contractors, or outsourced lead qualification support Benefits - 100% remote: so you can work where you feel most comfortable and inspired - Stay healthy: generous medical and dental for both you and your dependents - Relax and unwind: with plenty of paid vacation, and paid sick time for when you need it - Paid volunteer days: for you to spend giving back to non-profits/organizations that are important to you - Celebrate: we observe both US and Canadian holidays - and a whole week of rest in December - Family leave: paid time off for when your family grows - Save up: put pre-tax savings into a 401k/RRSP - we’ll match a portion of your contributions - Fitness fund: to help you feel your very best - Equipment fund: so you can deck out your home office - Monthly coffee budget: grab that latte - it’s on us - Learning and development: keep growing with paid courses, books, and conferences - Hang out: spend time together with your team virtually or in-person through culture events, Friday socials, and more - Pro tools: MacBook Pro (or Air) and all the tools you need to do a great job

About Gusto At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve. All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy. AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process. About the Role: Gusto is searching for a builder. Not a manager of an existing PEO sales team — a founder-minded sales leader who will design the motion, write the playbook, hire the team, and carry a personal book of business in the early months. This is a 0→1 opportunity to establish Gusto's PEO sales org from the ground up, and we're looking for someone who is energized by that challenge. You will drive new PEO revenue by selling Gusto's co-employment solution to both prospects and our existing base of 400,000+ customers — Gusto's single biggest competitive advantage over legacy PEOs. The pace is fast, the market opportunity is real, and we're looking for someone who will bring experience, creativity, and a genuine passion for building to the table every single day. You align with our company values and have a knack for building for the long haul. If you're excited to roll up your sleeves, lead by example, and architect something from scratch, let's talk. About the Team: You will be the founding leader of Gusto's PEO sales function. In the first 6–12 months, you'll operate as a true player-coach — personally closing deals while simultaneously building the team, tooling, and infrastructure around you. You'll define the ideal customer profile, build out the sales stages and pipeline architecture in Salesforce, and establish the channel strategy (including broker and accountant referral partnerships) that will drive scalable new business over time. This team will serve as Subject Matter Experts on PEO, guiding prospects through complex buying decisions and partnering closely with HR, benefits, and payroll counterparts to deliver a seamless customer experience. Your biggest unfair advantage: Gusto's existing install base. Like the best scaled PEOs, a meaningful share of your pipeline will come from converting existing payroll customers — and you'll be the one to design and build that on-ramp. Here’s what you’ll do day-to-day: - Sell and build simultaneously. For the first 6–12 months, carry a personal book of business while building the team and infrastructure around you. This is a player-coach role that requires someone comfortable operating at both levels. - Design the sales motion from scratch. Define sales stages, lead routing, funnel metrics, and pipeline architecture in Salesforce. This org doesn't have a pre-built RevOps foundation — you'll build it. - Own the full talent lifecycle. Partner closely with Recruiting to define hiring profiles, run interviews, and select top PEO sales talent. Onboard new hires for fast ramp and continuously assess team capacity to stay ahead of headcount needs. - Build and leverage the channel ecosystem. Develop a point of view on broker, GA, and accountant referral channels. Even if you don't own these relationships day one, you'll be expected to shape the strategy and lay the groundwork for a scalable partner channel. - Convert the install base. Develop the playbook for converting Gusto's existing 500K+ payroll customers to PEO. Understand the unique motion, objections, and value proposition for in-base selling vs. cold-start prospecting. - Operate with selling season fluency. Understand and plan around PEO's concentrated selling window (Sept–Dec, with ~50–60% of new business landing Jan 1). Build team capacity, pipeline targets, and go-to-market rhythms accordingly. - Collaborate cross-functionally with Sales, Marketing, and Product leadership to identify market opportunities, drive pipeline, and help shape PEO product strategy. - Use data to drive decisions — from advisor skill development to team-level initiatives. Track, measure, and report on sales effectiveness; adjust programs as needed. - Lead with AI fluency. As a people leader at Gusto, you're expected to actively model and drive AI adoption across your team — not just as a user, but as a champion. This means leveraging AI tools to surface pipeline insights, accelerate coaching, improve forecast accuracy, and identify at-risk deals earlier. You'll help your team integrate AI into daily workflows (outreach, call prep, follow-up), experiment with new tooling, and share learnings across the broader sales org. We expect our leaders to stay ahead of the curve and bring a point of view on how AI can make the team meaningfully better. - Build a culture of excellence. Cultivate each individual's skill set and guide career pathing as they grow within the organization. Ensure the team maintains deep knowledge of PEO compliance, co-employment regulations, and applicable state and federal employment law requirements. Here’s what we're looking for: - PEO Expertise: 5+ years of experience in PEO sales, with direct experience standing up a PEO sales org or building a sales team 0→1 in a high-growth environment. We're prioritizing builder profiles over tenure in a mature org. - Player-Coach Experience: Proven ability to carry personal quota while simultaneously building team, process, and infrastructure. This is not a pure management role in the early stages. - Selling Season Fluency: Direct experience operating within PEO's Jan 1 selling cycle — Sept–Dec pipeline build, renewal dynamics, and capacity planning. This is a key screen for PEO-specific operating experience vs. generic HCM. - Install Base Conversion: Experience developing or executing strategies to convert an existing customer base to a higher-tier or adjacent product. Familiarity with in-base PEO conversion motions is a strong plus. - Channel Strategy: Understanding of broker, GA, and accountant referral channels in the PEO or benefits space. Ability to develop a POV and lay groundwork for scalable partner-sourced pipeline. - RevOps & Pipeline Architecture: Experience building or significantly contributing to Salesforce pipeline design — sales stages, lead routing, funnel reporting — from an early-stage starting point. - Management Experience: 5+ years of people management in a sales organization, including direct involvement in recruiting and hiring. - Results-Oriented: Consistent track record of establishing and exceeding measurable goals. - Sales Acumen: Strong working knowledge of inbound and outbound sales methodologies in SMB SaaS or HCM/PEO environments. - Collaboration: Ability to work effectively across Sales, HR, Benefits, and Product teams; excellent interpersonal skills. - AI Leadership: Demonstrated ability to evaluate, adopt, and champion AI and automation tools in a sales environment. Comfortable going beyond personal usage — setting expectations, building habits, and holding the team accountable to AI-enabled ways of working. - Technical Proficiency: Salesforce.com (SFDC) experience required, including pipeline and funnel design; familiarity with HCM platforms and benefits administration tools preferred. Our target on-target earnings (OTE) compensation for this role is $270,000/yr to $280,000/yr in Denver & most remote locations, and $295,000/yr to $318,000/yr for San Francisco, & New York. This OTE is structured with a target 60% base pay and 40% commission pay with an uncapped commission structure. Final offer amounts and the exact base/commission split are determined by multiple factors including candidate location, experience, and expertise and may vary from the amounts listed above. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.