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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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.

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.