Strategic Account Executive (Sales Leader)

Strategic Account Executive (Sales Leader)

Seeking a first-rate sales leader focused on advancing UpSmith’s mission to combat the skilled worker crisis by driving workforce productivity for employers, starting with a focus in U.S. skilled trades.

Company Overview

UpSmith combats America’s 1 million skilled worker shortage in construction and manufacturing by building technology to improve workforce productivity. 

UpSmith deploys two products: 1) Upskill, a software product to source, screen, and train candidates based on their potential to become productive technicians in under 90 days, and 2) Boost, a software product increasing technician productivity by rewarding skilled workers for value-creating behaviors in the field. 

The Company is backed by a16z, Asymmetric Capital Partners, GSV Partners, and multiple strategic angels, including current and former executives at Uber, McKinsey, Thumbtack, Trilogy, Boeing, and General Electric.


  • Revenue Generation and Market Penetration:
    • Develop and execute a results-driven sales strategy to meet and exceed revenue targets (e.g. Series A ready by end of 2024).
    • Identify and cultivate new business opportunities through proactive prospecting, networking, and relationship building.
    • Manage the entire sales cycle, from lead generation to deal closure, ensuring a seamless and positive customer experience.
    • Drive 15%+ month on month revenue growth by strategically expanding UpSmith’s B2B enterprise clients and market share.
  • Strategic Account Development:
    • Identify and cultivate high-value strategic accounts to maximize long-term business partnerships.
    • Implement initiatives to increase customer value (measured by LTV/CAC) and satisfaction (measured by NPS, CSAT, and net dollar retention).
  • Sales Funnel Optimization:
    • Optimize the sales funnel by implementing targeted initiatives that accelerate the conversion of leads into paying customers.
    • Continuously assess and refine the lead generation and qualification processes for maximum efficiency.
  • Customer Obsession:
    • Deeply understand customer problems to be solved, implications of these problems on customer pain, and implied payoff of UpSmith’s solutions in resolving these issues and creating value for our customer.
    • Collaborate with operations teams to ensure seamless onboarding, adoption, and satisfaction for new customers.
    • Leverage customer feedback to drive product enhancements and improvements in close coordination with product and engineering.
    • Be the “voice of the customer” in internal discussion with UpSmith teammates, always raising the bar for our team in how we deliver for their needs.
  • Data-Driven Decision-Making:
    • Utilize data analytics to make informed decisions and adjust strategies for optimal outcomes.
    • Implement data-driven sales forecasting and reporting processes.
  • High Impact Contributor:
    • Lead by example as the primary sales representative, actively engaging with prospects, understanding their needs, and effectively conveying the value of UpSmith’s solutions to solve problems and create meaningful outcomes for their companies.
    • As the sales operation expands, recruit, onboard, and mentor a high-performing sales team, fostering a collaborative and results-driven culture within the sales organization.
  • Market Analysis:
    • Stay informed about industry trends, competitor activities, and market changes to inform sales strategies and product development.


  • Proven success in B2B SaaS sales, preferably in an enterprise environment with focus on strategic buyers from skilled trades platforms or private equity aggregators of skilled trades companies.
  • Demonstrated ability to build and maintain strong customer relationships, particularly as a senior executive level.
  • Excellent communication and presentation skills, including both verbal and written documents.
  • Strategic thinker with a results-oriented mindset and personal accountability for outcomes.
  • Previous experience in management consulting, investment banking, corporate development, and/or B2B sales leadership roles are a plus.


UpSmith compensates in the 75th percentile of Bay Area technology companies at similar levels of funding (<$10mm), regardless of where an employee chooses to live. This is a remote position.

  • Competitive cash + equity
  • Medical, dental, vision benefits
  • Opportunities for professional development and follow on awards 

How to Apply

Interested candidates are invited to submit their resume, along with a cover letter outlining their relevant experience and approach to B2B SaaS sales leadership. Please apply through our website or send applications to careers at

Learn more about UpSmith

UpSmith, Inc. is a technology venture on a mission to combat the skilled worker crisis.

This Account Executive role represents an opportunity to shape go-to-market activities for a stage team creating large-scale positive impact while generating substantial value in a $2T+ industry. 

UpSmith is based in Dallas, TX and brings a mission-driven culture grounded in five key values: Raise Expectations, Be an Owner, Bias for Action, Believe in People, and Commit.

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