Enterprise Account Executive
About The Position
UpKeep is seeking an Enterprise Account Executive to own a defined book of the company's largest and most strategic accounts. This role involves a consultative, multi-threaded sales approach for both existing customers and new prospects, focusing on building executive relationships, navigating complex buying committees, and driving significant Annual Recurring Revenue (ARR) through larger, longer-cycle deals. The Enterprise Account Executive will partner with Customer Success to expand existing accounts and with Business Development and Marketing to acquire new enterprise logos through account-based outbound strategies. Success in this role is measured by the ability to drive meaningful ARR, not by call and email volume.
Requirements
- 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.
- Proficiency with CRM applications such as Salesforce.
- Ability to leverage AI to help manage workload and 10X output.
- 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.
Nice To Haves
- Maintenance, Manufacturing, and Facilities industry experience a strong plus.
- Bachelor's Degree or equivalent experience is a plus.
- Experience with modern sales tooling — e.g., Gong, Outreach, ZoomInfo.
Responsibilities
- Own a defined list of strategic customer accounts and drive expansion, upsell, and multi-site/enterprise-wide adoption.
- Partner with Customer Success Managers to build joint account plans, identify whitespace, and convert usage into commercial growth.
- Develop and maintain executive relationships to elevate UpKeep from a departmental tool to an enterprise standard.
- Build and manage a pipeline of expansion opportunities to meet growth quotas 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 execute coordinated, multi-touch outbound plays.
- Multi-thread across the buying committee, engaging economic buyers, champions, and technical stakeholders.
- 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.
- Own complex, multi-stakeholder contract negotiations and close deals.
- Develop deep product, industry, and competitive expertise to articulate a differentiated value proposition and quantifiable business case.
- Maintain accurate records in Salesforce, including pipeline, activity, forecast, and account intelligence.
- Forecast accurately against assigned account metrics and prepare account/pipeline reports.
- Collaborate cross-functionally to identify and grow opportunities.
- Contribute to the enterprise playbook by surfacing effective strategies and flagging challenges.
Benefits
- Competitive base salary + benefits
- Meaningful ownership (equity)
- Benefits that support your health, focus, and long-term growth
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
