Enterprise Account Executive

UpKeep•Los Angeles, CA

2d•$120,000 - $240,000•Remote

About The Position

UpKeep is seeking an Enterprise Account Executive to manage a portfolio of the company's largest and most strategic accounts. This role involves a consultative, multi-threaded sales approach targeting both existing customers for expansion and net-new prospects through account-based outbound efforts. The position focuses 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 grow existing accounts and with Business Development and Marketing to acquire new enterprise clients, owning the strategy, relationships, commercial negotiations, and sales targets for their assigned accounts.

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 manage workload and increase 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, is a plus.

Responsibilities

Own a defined list of strategic customer accounts and drive expansion, upsell, and enterprise-wide adoption.
Partner with Customer Success Managers to build joint account plans, identify opportunities, and convert usage into commercial growth.
Develop and maintain executive relationships to position UpKeep as an enterprise standard.
Build and manage a pipeline of expansion opportunities to meet growth quotas within the customer base.
Own a focused list of target prospects and drive new-logo acquisition through account-based selling.
Partner with Business Development Representatives and Marketing to execute coordinated 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, complex enterprise sales cycle.
Conduct deep account research and deliver tailored, 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 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.
Own personal and departmental targets aligned with company objectives.
Contribute to the enterprise sales playbook by surfacing successes, challenges, and helping codify repeatable processes.