Enterprise Account Executive, UpKeep

• 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

Desirable

• 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
• 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