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.

About the Role

We're looking for our new Head of Accountant Community to build and scale Gusto's brand presence and community with the accountant audience.

This is a highly visible, strategic role responsible for representing Gusto externally to accountants through thought leadership, community programs, events, and partnerships. You'll create the connective tissue between brand, community, and growth—driving firm recruitment, activation, and long-term engagement while strengthening Gusto's reputation as the small business partner accountants trust and advocate for.

About the Team

This role is part of the go-to-market team responsible for driving pipeline and fueling growth across indirect channels. We combine creativity, data-driven insights, and cross-functional collaboration to design campaigns that reach, engage, and convert the right audiences at scale. Together, we've helped Gusto grow to serve thousands of accounting partners nationwide, and we're just getting started.

Here's what you'll do day-to-day

● Build and lead Gusto's accountant community strategy, defining how we show up consistently and credibly across owned, earned, and experiential channels.

● Represent Gusto externally to the accountant audience through thought leadership, speaking opportunities, events, community programs, and industry partnerships.

● Develop and scale community programs and experiences (virtual and in-person) that foster connection, education, and advocacy among accounting firms.

● Own and evolve Gusto's accountant-facing thought leadership strategy, partnering with content, comms, and product marketing to create narratives that build trust and authority.

● Partner closely with product, marketing, and sales teams to ensure community efforts translate into firm recruitment, activation, and engagement.

● Design and execute events and sponsorship strategies (e.g., conferences, field events, roundtables, meetups) that strengthen brand affinity and accelerate funnel impact.

● Collaborate with PR, comms, and social teams to amplify community voices and elevate Gusto's presence in the broader accounting ecosystem.

● Establish feedback loops with accountants to surface insights that inform product positioning, messaging, and partner experience.

● Define and track success metrics across accountant community health, including awareness, sentiment, engagement, and top-of-funnel performance.

● Manage budgets, vendors, and external partners to deliver high-quality programs efficiently and at scale.

Here's what we're looking for

● 7–10 years of experience in community marketing, ideally within partner- or relationship-driven industries.

● Proven experience building and scaling communities or external-facing programs that drive trust, engagement, and long-term growth.

● Strong track record of representing a brand externally through events, speaking, partnerships, or thought leadership.

● Experience developing integrated programs that connect brand and community efforts to measurable business outcomes.

● Excellent storytelling and communication skills, with the ability to craft compelling narratives for senior, professional audiences.

● Strong cross-functional collaborator who can influence without authority and partner closely with sales, product marketing, comms, and leadership.

● Data-informed mindset with experience defining and measuring success across brand, engagement, and funnel metrics.

● AI fluency: Ability to use AI tools (e.g., ChatGPT, Glean) to improve efficiency in content creation, personalization, and insight generation, with strong judgment about when to apply AI vs. human expertise in community building.

● Comfort operating in a fast-paced, ambiguous environment while building something net-new from the ground up.

● Bonus: experience marketing to accountants, professional services firms, or other referral-based ecosystems.

Compensation

Our cash compensation amount for this role is $152,655/yr to $190,000/yr in Denver, Phoenix/Scottsdale, Las Vegas, Chicago, and Atlanta; $180,000/yr to $225,000/yr for San Francisco & New York, and CAD $147,000 to $180,000/yr for Toronto. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

#LI-HYBRID

Transform Your Career 

We deliver unparalleled opportunities for growth and career advancement. Our dynamic, entrepreneurial culture supports your journey every step of the way. 

Embrace new challenges and deliver real value to some of the world’s most influential Fortune 100 brands, growth companies transforming their industries, and mid-market firms that need help navigating the defining moments of their lifecycle. Work side by side with business leaders to solve complex client challenges and make a true impact. Love what you do as part of a diverse organization committed to collaboration and continuous learning. 

The Team - Accounting Advisory 

Our team is comprised of a powerful mix of seasoned professionals with public accounting experience and business consultants with a deep expertise in a broad range of industries. We take a comprehensive approach to helping clients navigate through the IPO process, M&A lifecycle support, and leverage our own Technical Accounting Solution Center to address critical financial reporting and technical accounting issues for clients. 

Your Impact 

• Support fast growing companies and well-known enterprises (both publicly traded and privately held) on a wide variety of projects including: IPO preparation, transaction support, carve-outs and/or spin-offs, audit readiness, and adoption of new accounting pronouncements.
• Engage with clients and colleagues on technical accounting related issues to provide research-based guidance, technical accounting documentation and give recommendations for potential solutions.
• Create and deliver presentations on technical concepts, project work plans, delivery approach, milestones, and results to client stakeholders.
• Review team progress to ensure compliance with work program and professional standards.
• Educate internal and external audiences on Accounting Advisory best practices.
• Identify, design and implement creative business solutions to continually improve the firm’s methodology and approach.
• Establish credibility as a trusted advisor.
• Manage client relationships with an eye toward identifying and closing on new business opportunities.
• Actively participate in career development activities and technical training of staff. 

Your Experience 

Minimum Qualifications 

• Bachelor’s degree in Accounting.
• CPA and/or CMA (Certified Management Accountant).
• 8+ years of recent professional services experience (public accounting or advisory firm) is strongly preferred; directly relevant technical accounting/financial reporting experience with a publicly held/Fortune 500 organization may be considered in its place.
• Strong knowledge of SEC reporting, U.S. GAAP and SOX standards.
• Demonstrated knowledge of accounting/audit practices, procedures and reporting standards.
• Flexibility to travel 

Preferred Qualifications 

• Master's in Accounting. 
• Knowledge of common Enterprise Resource Planning (ERP) and accounting systems (i.e., Oracle, SAP, PeopleSoft, JD Edwards, Workday, NetSuite, Microsoft Dynamics 365).
• Proven ability to lead, motivate and build teams that deliver services and solutions that surpass client expectations.
• Previous experience leading and executing complex projects in challenging environment 

#LI-Hybrid

Company Overview

Asset Living is a third-party management firm and a proven partner in fostering thriving communities nationwide. Founded in 1986, Asset Living has decades of experience delivering exceptional value to our partners. Since the beginning, our undeniable passion has driven our organic growth from a small property management firm to one of the most trusted allies in real estate. Asset Living's growing portfolio includes a multitude of properties across the country that span the multifamily, single-family home rentals, affordable housing, build-to-rent, active adult, and student housing divisions.   

Asset Living is a fast-growing company made up of talented individuals from diverse backgrounds that differentiate us and help us drive innovation and results for our clients and communities across the US. At Asset Living, we wholeheartedly believe 'Together We Lead, Together We Succeed. We empower each other to lead by example, collaborate, and evolve – inspired by our belief that we can continually improve as individuals and as an organization. Together, we create an environment where every voice is heard, every idea is valued, and every individual experiences opportunities to grow as our company grows. When you join Asset Living, you become part of a dynamic team that thrives on unity, unique talents, and a universal culture of winning.    

Recognized as one of the nation's Best and Brightest Places to Work and ranked in the NMHC top 50 professionals, join Asset Living because of its reputation as the most trusted partner in real estate, workplace culture, and growth opportunities. Asset Living is a member of The Institute of Real Estate Management (IREM) and is recognized as an Accredited Management Organization (AMO). Together, we lead the way, and together, we achieve excellence in all that we do. Join a workplace where success is a collective journey and leadership is a shared responsibility.   

Senior Accountant

The Senior Accountant is responsible for many aspects of financial reporting and will work directly with the Assistant Controller to develop new processes and procedures.

Essential Duties & Responsibilities

• Initiate and post journal entries, prepare balance sheet account reconciliations, and research & resolve issues as needed
• Prepare monthly financial reporting packages for one or more regional offices, including performing variance analysis
• Research accounting guidance and prepare memos
• Assist in development of new processes and procedures to improve month end close and financial reporting, and improve coordination between property accounting and corporate accounting
• Assist in departmental initiatives to improve efficiency and utilization of available tools, including newly implemented ERP
• Analyze expenses and assist in budget preparation
• Prepare audit related requests and other duties as assigned

Education & Experience

• Bachelor and/or Master’s Degree. Preference in Accounting or Finance
• Multifamily property accounting experience preferred
• Excellent critical reasoning, quantitative, and analytical skills
• Deep understanding of financial concepts
• Excellent interpersonal, written and verbal communication skills
• Proven organizational skills with attention to detail

This job description should not be considered all-inclusive. It is merely a guide of expected duties. The employee understands that the job description is neither complete nor permanent and may be modified at any time. At the request of their supervisor, an employee may be asked to perform additional duties or take on additional responsibilities without notice. This is a safety-sensitive position and may be subject to additional compliance requirements.

#LI-Hybrid

Hi, we're Oscar. We're hiring a Senior Manager, Technical Accounting to join our Accounting team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

Senior Manager, Technical Accounting, would lead our technical accounting work. You will work cross-functionally to understand and to provide technical accounting guidance on new or complex transactions and corresponding financial disclosures. You will develop, enhance, and maintain accounting policies and ensure policies reflect current practices and operations of the business and are up-to-date and compliant with existing and newly adopted accounting standards and regulations.

You will report into the Associate Director, SEC Reporting and Technical Accounting.

Work Location: 

This is a remote position, open to candidates who reside in: Atlanta, GA. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $134,136 - $176,053 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Lead our technical accounting work required under US GAAP and statutory reporting and partner with the Tax Team to ensure tax aspects are considered.
• Partner with teams, and external partners and/or consultants, to:
  • provide technical accounting expertise to support new transactions and new or evolving business arrangements, and
  • prepare technical accounting analysis on complex accounting issues.
• Create our accounting policies.
• Oversee, and apply new accounting pronouncements applicable to the Company.
• Work with the Company's external auditors on technical accounting matters.
• Help review financial disclosures in SEC and statutory filings related to our accounting policies and impact of new accounting pronouncements.
• Develop relationships with cross-functional teams to understand broad goals and provide accounting guidance and best practice recommendations to allow process improvements.
• Perform ad-hoc technical accounting research and analysis to support special projects.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 6+ years of relevant experience.
• Bachelor's degree in Accounting, Finance, or related field, or 4 years of relevant experience.
• Certified Public Accountant licensure (CPA).
• 2+ years of experience with US-based insurance companies.
• 2+ years of practical experience in financial reporting.

Bonus points:

• Experience in a similar position at a health insurance company.
• Experience working collaboratively across the organization.
• 4+ years of experience with US-based insurance companies.
• 4+ years of practical experience in financial reporting.
• 6+ year in public accounting

Hi, we're Oscar. We're hiring a Senior Accountant, Statutory and Legal Entity Reporting to join our Finance Ops & Accounting.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Associate, Financial Reporting is responsible for execution of statutory legal entity reports. This includes the preparation of statutory financial exhibits and footnotes, analytics, audited financial statements and supplemental filings.

You will report into the Associate Director, Financial Reporting.

Work Location: This is a remote position, open to candidates who reside in: Atlanta, GA. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $82,717 - $108,566 per year.You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Monthly, quarterly and annual financial reporting
  • Completing the monthly, quarterly, and annual statutory (and stand-alone legal entity) reporting processes, including analytics and related financial statement disclosures.
  • Executing work related to the statutory audit efforts.
• Work on process improvement opportunities.
• Work with Regulatory Relations and other teams across the Organization to respond timely to regulator inquiries.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• Bachelor's degree in Accounting, Finance, or related field, or 4 years of relevant experience.
• 3+ years of related experience on an accounting or reporting team.

Bonus points:

• Experience in a similar position at a health insurance company.
• Experience with US-based insurance companies.
• Certified Public Accountant licensure (CPA).
• Practical experience in statutory reporting.

Hi, we're Oscar. We're hiring an Associate, Tax to join our Accounting organization.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Tax Associate is responsible for income tax compliance including preparation of tax provisions under Generally Accepted Accounting principles (GAAP) and Statutory reporting,  and supports the federal, state and local tax return processes. This role also supports tax planning and projects.

You will report into the Senior Director, Tax.

Work Location: This is a remote position, open to candidates who reside in: Atlanta, GA. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $87,000 - $114,000 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

• Prepare annual and quarterly GAAP and Statutory tax provisions.
• Assist with the preparation and review of the  U.S. federal, state, and local tax returns as well as estimates and payments for the corporate holding company and insurance subsidiaries.
• Prepare tax forecast modeling. 
• Prepare monthly tax journal entries and  quarterly tax reconciliations.
• Assist with sales and use, and other indirect tax compliance functions.
• Maintenance and timely adherence to tax compliance calendar.
• Prepare financial data, analysis and modeling to support tax projects.
• Prepare audit and notice responses. 
• Work closely with areas of Finance and the business to support other tax compliance and planning projects as needed.
• Identity and implement process improvements.

Requirements:

• 4+ years of tax experience in a public accounting firm or equivalent experience in a corporate tax department.
• Bachelor’s degree preferably in Accounting or 4 years commensurate experience.

Bonus points:

• CPA and/ or Master’s of Taxation.
• Experience with preparation of the corporate tax provision.
• Insurance experience.
• Statement of Statutory Accounting Principle (SSAP) 101 tax reporting.
• Experience implementing tax provision software.

Submit your interest to join our Partner Sales team!

Gusto is seeking sales professionals who thrive in a fast-paced, consultative environment and are interested in being considered for future start dates in 2026. In these roles, you will own each partner relationship from first conversation to lasting collaboration—delivering exceptional experiences and driving meaningful results for accounting firms or financial advisors and their clients. If you’d like to be considered for future opportunities with our team, please complete the form below and upload your resume. 

While start dates are still being determined for 2026, we’d love to connect! Does this sound like you? Apply below!

About the Role:

Gusto’s Partner Sales organization is growing, and we’re always looking to meet future teammates who are passionate about helping accountants and financial advisors transform the way they serve small businesses. Whether your strengths lie in acquiring new partnerships or nurturing long-term relationships, we’d love to connect.

Our GustoPro Sales team partners with accounting firms and financial advisors nationwide to help them onboard their clients to Gusto and unlock the full value of our platform. We’re building a talent pipeline for future Account Executive and Account Manager opportunities—both roles focused on empowering our accountant partners and financial advisors, driving adoption, and growing shared success across the Gusto ecosystem.

Here’s what you’ll do day-to-day:

• Nurture Partner Relationships: Build and manage trusted relationships with accounting firm partners. Grow existing relationships by helping firms activate more clients and deepen their engagement with Gusto.
• Develop & Close Business: Drive new business by identifying, engaging, and onboarding new firms into the Gusto Pro ecosystem.
• Empower Partners: Lead consultative conversations that uncover partner needs and align Gusto’s solutions to their business goals.
• Collaborate Cross-Functionally: Work closely with Marketing, Product, and Customer Success to improve the partner experience.

Positions available in the future range across multiple levels. Here’s what we're looking for:

• 5+ years of professional sales experience in payroll, HCM, SaaS, or HR tech with a focus on accounting firms or financial advisors.
• 2+ years of proven success managing or acquiring a book of business with measurable quota attainment.
• Experience working with accountants, financial advisors, payroll, HR tech, or financial services.
• Skilled in consultative, relationship-based sales and value-driven conversations.