Enterprise Account Executive

About this role

We’re building the AI-powered future of maintenance.

UpKeep is on a mission to reinvent how the physical world runs—starting with the frontline teams who maintain it. We’re the creators of the world’s first AI-first CMMS (Computerized Maintenance Management System), equipping technicians and facilities teams with automation, machine learning, and predictive insights that drive operational speed, safety, and efficiency.

What started as a garage-built prototype is now a fast-scaling SaaS company, backed by Insight Partners, Emergence Capital, and Y Combinator. Over 4,000 companies—including Shell, Yamaha, Unilever, and Marriott—run on UpKeep to modernize their asset operations. We’re leading the $30B category shift toward Asset Operations Management , where uptime, intelligence, and AI converge.

Why join us:

• Own the AI-first transformation of an entire industry. Every feature we ship leverages AI—from predictive work orders to sensor-driven automations. You’re not just iterating—you’re pioneering how data reshapes physical operations.

• Real traction, real scale. Recognized as Gartner’s #1 Facility Management solution and G2’s top-rated CMMS, we’ve earned market leadership through product, not puff.

• A company where builders thrive. We move fast, optimize for outcomes, and give high-agency operators the autonomy to ship big things. Our culture rewards bold thinking, not bureaucracy.

• Global team, local energy. With 100+ employees across the world, we support remote-first work with deep investment in our LA HQ—where certain roles and leadership converge for rapid innovation.

• Equity and upside, not just a paycheck. Competitive comp, meaningful ownership, and benefits that support your health, focus, and long-term growth.

If you’re driven by impact, energized by AI, and hungry to transform a legacy industry—we’re hiring!

POSITION SUMMARY

The Enterprise Account Executive owns a defined book of UpKeep's largest and most strategic accounts, running a consultative, multi-threaded sales motion across both existing customers and net-new prospects. This is a lower-volume, higher-value role: success is measured by the ability to build executive relationships, navigate complex buying committees, and drive meaningful ARR through larger, longer cycle deals not by call and email volume.

The role runs two connected motions. On the customer side , you will partner closely with Customer Success to grow and expand a named list of strategic accounts, turning satisfied customers into enterprise wide deployments. On the prospect side , you will partner with Business Development and Marketing to land UpKeep's largest target accounts through coordinated, account-based outbound. In both cases you own the strategy, the relationships, the commercial negotiation, and the number.

ESSENTIAL FUNCTIONS AND RESPONSIBILITIES

Grow & Expand — Named Strategic Customers

• Own a defined list of strategic customer accounts and drive expansion, upsell, and multi-site / enterprise-wide adoption within them.

• Partner tightly with Customer Success Managers to build joint account plans, identify whitespace, and convert healthy usage into commercial growth.

• Develop and maintain executive relationships that elevate UpKeep from a departmental tool to an enterprise standard.

• Build and manage a pipeline of expansion opportunities that ensures you hit your growth quota within the customer base.

Land & Win — Strategic Prospects

• Own a focused, named list of UpKeep's largest target prospects and drive new-logo acquisition through account-based selling.

• Partner with Business Development Representatives and Marketing to build and execute coordinated, multi-touch outbound plays into these accounts.

• Multi-thread across the buying committee — identifying and engaging economic buyers, champions, and technical stakeholders across the organization.

• Build the pipeline required to consistently achieve new-business quota targets in a longer, more complex enterprise cycle.

Own the Deal & the Number

• Conduct deep account research and deliver tailored, consultative, executive-level product demonstrations that connect UpKeep to strategic business outcomes.

• Own complex, multi-stakeholder contract negotiations and close deals before a structured handoff to Customer Success and Implementation.

• Develop deep product, industry, and competitive expertise to articulate a differentiated value proposition and quantifiable business case.

• Maintain accurate, disciplined records in Salesforce — pipeline, activity, forecast, and account intelligence.

• Forecast accurately against assigned account metrics; prepare account and pipeline reports; collaborate cross-functionally to identify and grow opportunities across the territory.

• Own personal and departmental targets aligned to company objectives, and clearly communicate progress on quarterly initiatives to internal and external stakeholders.

• Contribute to the enterprise playbook — surface what's working, flag what isn't, and help codify a repeatable process as the motion matures.

EXPERIENCE

• 5+ years of B2B SaaS sales experience, with a track record in large account selling.

• Demonstrated success owning complex, multi-stakeholder deals with larger ACVs ($100K+) and longer sales cycles.

• Experience selling into and expanding large, multi-site organizations; comfort engaging at the executive level.

• Proven track record of meeting or exceeding quota and earning strong customer trust.

• Comfort operating in an undefined, greenfield environment where the process is still being built.

• Maintenance, Manufacturing, and Facilities industry experience a strong plus.

• Bachelor's Degree or equivalent experience is a plus.

KNOWLEDGE

• Proficiency with CRM applications such as Salesforce. Looking for someone that leverages AI to help manage your workload and 10X your output!

• Experience with modern sales tooling — e.g., Gong, Outreach, ZoomInfo, is a plus.

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