Own a strategic Mid-Market territory and drive new-business and expansion revenue through account strategy, consultative selling, executive engagement, and complex deal execution. Responsibilities include territory planning, pipeline generation, forecasting, multi-threaded stakeholder management, value-based discovery, business-case development, procurement navigation, CRM discipline, and identifying expansion opportunities. The role also mentors peers, raises sales standards, and partners cross-functionally to improve win rates and deal velocity.
Employ is transforming how hiring gets done. With our three ATS solutions - Jobvite, Lever, and JazzHR - plus cutting-edge AI Companions, we free recruiters from admin work and give them more time for what matters: connecting with people. More than 26,000 global customers rely on Employ to make millions of candidate connections each year, helping them hire smarter, faster, and at scale. From growing startups to the world’s most recognized brands, we’re redefining what’s possible in talent acquisition.
We’re a fast-moving, remote-first team of builders and innovators who live our people-first philosophy every day. We back it up with flexible work scheduling and paid time off, comprehensive benefits, and career development opportunities that help you thrive. At Employ, you won’t just grow your career - you’ll help millions of others grow theirs.
Come join our team where we have each other’s backs, champion our customers, hold ourselves accountable, and shape what’s next in talent acquisition.
Candidate Safety Notice
Please note, employ takes candidate safety seriously. Employ recruiters and employees communicate only via official @employinc.com email addresses. We will never request payment or personal financial information during the hiring process. If you receive suspicious outreach claiming to be from Employ, please report it to [email protected].
About the Opportunity – Principal Mid-Market Account Executive:
This is a strategic individual contributor role designed for top-performing Mid-Market sellers who operate with enterprise-level rigor inside the Mid-Market segment.
As a Principal Mid-Market Account Executive, you are expected to be a business partner to your customers, a strategist within your territory, and a standard-setter within the sales organization. You bring a repeatable, insight-driven approach to winning complex deals, and you elevate those around you through your execution and thinking.
You will own a high-value Mid-Market territory and be responsible for driving durable revenue through account strategy, multi-threading, and disciplined deal execution, while also influencing broader sales excellence.
About the Team:
You’ll be a part of a high-performing Mid-Market sales team focused on driving new business growth through disciplined outbound execution and consultative selling. This is a metrics-driven, high-activity environment where accountability, coaching, and continuous improvement are core to success. The team is deeply collaborative and plays a critical role in scaling pipeline, revenue, and repeatable sales performance across the organization.
What You’ll Do:
- End-to-end ownership of a strategic Mid-Market territory with clear coverage, segmentation, and whitespace strategy.
- Delivery of predictable, high-quality revenue across new business and expansion.
- Forecast accuracy at a high confidence level (commit discipline, low variance).
- Elevation of team standards through informal leadership, deal collaboration, and best practice sharing.
- Build and execute a multi-quarter territory strategy grounded in data, ICP alignment, and account prioritization Drive pipeline through account-based motions, executive outreach, and strategic prospecting (focused on quality and conversion, not volume alone).
- Lead deep, hypothesis-driven discovery that connects business objectives to measurable outcomes.
- Orchestrate multi-threaded deal cycles, building alignment across HR, TA, Finance, IT, Procurement, and executive sponsors.
- Develop and execute comprehensive deal strategies (stakeholder mapping, competitive positioning, risk mitigation, mutual close plans).
- Deliver executive-level narratives and business cases that quantify ROI and drive urgency.
- Navigate complex procurement, legal, and security processes with control and momentum.
- Identify and create expansion pathways early, positioning for land-and-expand success.
- Maintain exceptional pipeline hygiene, inspection readiness, and CRM discipline
- Partner cross-functionally to increase win rates and deal velocity.
- Act as a thought partner and mentor to peers on deals, discovery, and strategy.
- You operate with strategic intent across your territory, not just deal-to-deal execution.
- You bring consistency and predictability quarter over quarter.
- You excel at executive selling and value articulation tied to business outcomes.
- You proactively identify, surface, and mitigate deal risk early.
- You demonstrate strong internal influence without formal authority.
- You improve team performance by raising the bar on deal quality and thinking.
What Differentiates a Principal Account Executive:
What You Bring:
- 7–10+ years of quota-carrying SaaS sales experience.
- Sustained track record of top-tier performance (e.g., President’s Club, top 10–20%) in Mid-Market or Commercial segments.
- Demonstrated success closing complex, multi-stakeholder deals with meaningful ACVs.
- Advanced capability in territory strategy, account planning, and pipeline construction.
- High level of forecast accuracy and inspection rigor.
- Expertise in value-based, consultative sales methodologies (SPICED, MEDDICC, Command of the Message, or similar).
- Strong executive presence with the ability to influence VP and C-level stakeholders.
- Proven ability to self-inspect deals and continuously refine approach.
- High ownership, strong business acumen, and disciplined execution. Preferred Experience:
- Experience selling SaaS in HR Tech, Talent Acquisition, or adjacent markets.
- Experience managing platform or multi-product sales motions.
- Exposure to land-and-expand strategies within Mid-Market accounts.
Why You’ll Love Working Here:
Make an impact: Your work will directly shape how thousands of employees experience total rewards at Employ — ensuring programs that attract, engage, and retain top talent across the globe.
Meaningful, mission-driven work: Join a team where operational excellence in HR directly supports Employ’s mission to improve hiring outcomes for both people and businesses.
Remote-first culture: Work from where you’re most productive while staying connected to a collaborative, high-energy team through virtual-first rituals and regular in-person meetups.
Unlimited PTO: Trust-based time off so you can recharge and bring your best self to work.
Comprehensive benefits: Medical, dental, and vision coverage to support you and your family’s health and well-being.
Learning & development programs: Access to training, mentorship, and development resources to grow your skills — from HR operations to total rewards strategy.
At Employ, we believe that when people from different backgrounds and perspectives come together, amazing things happen. We’re proud to be an Equal Opportunity Employer, and we’re committed to creating an environment where everyone feels welcomed, respected, and able to thrive.
We do not discriminate based on race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law. We believe that when people feel they belong, they can do their best work and we want every member of our team to feel that sense of belonging.
If you need accommodation at any stage of the hiring process, please reach out. We’ll be glad to support you.
Recruitment Fraud Notice:
Employ takes candidate safety seriously. Please be aware that Employ recruiters and interviewers will only communicate with candidates using official email addresses ending in @employinc.com.
We will never ask for payment, banking information, or personal financial details at any stage of the hiring process, and we do not conduct interviews via messaging apps or social media platforms.
If you receive communication that appears suspicious or claims to represent Employ but does not come from an @employinc.com email address, do not respond or continue engaging with the sender. Please report the message to [email protected].
Similar Jobs
Cloud • Information Technology • Productivity • Security • Software • App development • Automation
Serve as a pre-sales technical expert for DX, partnering with Account Executives throughout the sales cycle. Lead technical discovery, evaluations, proof-of-concepts, pilots, product demonstrations, and solution design involving APIs and client engineering workflows. Advise prospects on deployment and analytics integrations, translate technical concepts into business value, and relay customer feedback to Product and Engineering teams. Manage technical follow-ups across multiple opportunities.
Top Skills:
APIsCi/CdGitGithub CliRestRubyRuby On RailsSQL
Cloud • Information Technology • Productivity • Security • Software • App development • Automation
Own portfolio-level technical programs spanning product, engineering, GTM, finance, legal, security, and IT. Lead complex launches, migrations, integrations, monetization initiatives, and enterprise transformations; resolve ambiguity, manage dependencies and risks, influence executives, establish governance mechanisms, measure business impact, and mentor program managers. The role requires driving outcomes across multiple teams and time horizons without formal authority.
Top Skills:
Agile MethodologiesCloud TransformationData AnalyticsSoftware Development
Artificial Intelligence • Healthtech • Insurance • Machine Learning • Payments
Drive enterprise SaaS and services sales to health insurance plans within an assigned territory. Responsibilities include prospecting, nurturing, and closing high-value opportunities; delivering customized presentations and product demonstrations; exceeding revenue targets; tracking pipelines and forecasts in HubSpot; and communicating AI platform value, ROI, and payer-market insights to health plan executives.
Top Skills:
AIData ScienceHubspot CrmLlmsSaaS
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
