Enterprise Account Executive at UpKeep

Matcha; Northern (KY); Hybrid; USD 120,000 - 240,000; Full time

Benefits offered by this job

Equity

Job summary

UpKeep is seeking an Enterprise Account Executive to own a defined book of its largest accounts, leading a consultative, multi-threaded sales motion across existing customers and net-new prospects.

In this role you will grow with Customer Success and Marketing to drive ARR, while partnering with Business Development for targeted outbound and executive-level engagements. You will manage negotiations, forecast, and build a scalable enterprise sales motion.

Qualifications

• 5+ years of B2B SaaS sales experience with large ACVs and long cycles.
• Proven track record meeting or exceeding quota and earning trust.
• Experience selling into and expanding large multi-site organizations at executive level.
• Bachelor's Degree or equivalent experience is a plus.

Responsibilities

• Own defined strategic accounts and drive expansion and multi-site adoption.
• Build joint account plans with Customer Success and identify whitespace.
• Develop executive relationships to position UpKeep as enterprise standard.
• Close deals and conduct complex negotiations, handoff to CS.

Skills

Account-based selling

Executive relationship management

CRM (Salesforce)

Multi-threaded sales

Negotiation

Education

Bachelor's Degree or equivalent experience

Tools

Salesforce

Gong

Outreach

ZoomInfo

Job description

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.
• Strong account-based selling, territory planning, and pipeline generation skills in a strategic-sales environment.
• Consultative, value-based selling with the ability to build and defend a business case to senior stakeholders.
• Excellent written and verbal communication; strong organization, follow-up, and attention to detail.
• Ability to work independently and cross-functionally in a highly dynamic, fast-paced environment.

DESIRED BEHAVIORS

• Builder's mindset — thrives amid ambiguity, creates structure where none exists, and treats an undefined process as an opportunity rather than an obstacle.
• Receptive to change — flexible; seeks and adopts improved approaches and processes.
• Initiates action — results-oriented; takes ownership of actions and outcomes, meets commitments, and strives for high performance.
• Manages the workload — makes timely decisions, prioritizes effectively, solves problems, monitors results, and takes remedial action where necessary.
• Technically proficient — knows the role and has solid familiarity with tasks and responsibilities.
• Takes responsibility for own learning — knows personal strengths, recognizes development needs, is open to feedback, and always seeks to learn.
• Communicates ideas — strong facilitation and written communication; proposes a way forward and takes in diverse perspectives.
• Works collaboratively — shares information, fosters teamwork, and contributes to a positive work environment.
• Displays ethical character and competence — acts with integrity and intent, is accountable, and behaves according to company values.
• Acts as a good citizen of UpKeep.

COMPENSATION

This role will receive a competitive base salary + benefits. A variety of factors are considered when determining someone’s compensation–including a candidate’s professional background, experience, and location. Final offer amounts may vary from the amounts listed below.

The pay range for this role is $120,000/$120,000 - OTE $240,000 USD per year.

Company History & Product:

UpKeep started in a garage, where our founder Ryan taught himself to code and built the first mobile-first maintenance app. The idea was simple but powerful: put modern software in the hands of frontline technicians—and transform how maintenance gets done.

Today, UpKeep is the leading cloud-native Asset Operations Management platform, serving over 4,000 businesses worldwide across manufacturing, utilities, healthcare, and beyond. Our Industrial IoT and AI-first software helps maintenance and facilities teams streamline work, predict failures, and act faster—with real-time insights and automation at their fingertips.

We’re building for the deskless workforce—the essential workers who keep our physical world running—and arming them with the tools they deserve. In a world re-shoring manufacturing, accelerating automation, and embracing AI at scale, we’re riding the next macro wave—and leading the transformation of legacy maintenance into intelligent operations.

Backed by $50 million from Insight Partners,Emergence Capital,Mucker, andY Combinator,we're not just building software. We're defining a new category for the built world.Learn More!www.upkeep.comwww.upkeep.com/careersAt UpKeep, we celebrate and support our differences. We know employing a team rich in diverse thoughts, experiences, and opinions allows our employees, our products, and our community to flourish. UpKeep is honored to be an equal opportunity workplace. We are dedicated to equal employment opportunities regardless of race, color, ancestry, religion, sex, national orientation, age, citizenship, marital status, disability, gender identity, sexual orientation or Veteran status.