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Sales Executive

Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60290, USA
Listing for: Estateably
Remote/Work from Home position
Listed on 2026-03-01
Job specializations:
  • Sales
    Business Development, Sales Development Rep/SDR, B2B Sales, Sales Representative
  • Business
    Business Development
Salary/Wage Range or Industry Benchmark: 80000 - 100000 USD Yearly USD 80000.00 100000.00 YEAR
Job Description & How to Apply Below

Overview

We’re looking for a highly driven Sales Executive with a passion for technology and a proven ability to win in competitive SaaS markets. You’ll be selling a rapidly evolving solution where agility, resourcefulness, and tech-savviness are critical to success. If you thrive on outsmarting larger competitors, excel at crafting compelling presentations, and get excited about leveraging modern sales tools to win, this role is for you.

What

You’ll Do
  • Own and manage sales cycles, from prospecting to closing.
  • Become an expert in our product and industry, positioning us as the best solution for our customers’ needs.
  • Collaborate with our team to refine our sales playbook and improve processes.
  • Use data and feedback to improve your performance continuously.
  • Develop and execute strategic account plans to penetrate new markets and expand existing relationships.
  • Maintain accurate forecasts and sales activity reports in Hub Spot.
  • Stay up to date with industry trends, competitors, and market conditions.
  • Represent Estateably at industry conferences and events.
  • Consistently meet and exceed quota, driving revenue growth for the company.
Requirements
  • 2+ years in a B2B SaaS environment.
  • A strong track record of exceeding targets.
  • Eager learner of new tools and technology, excited about leveraging automation and AI.
  • Strong communication and presentation skills—you can clearly articulate value and build trust.
  • Coachable, data-driven, and always looking to improve.
  • Passionate about technology and solving customer problems.
  • Resilient and self-motivated—you thrive in a fast-paced, startup environment.
  • Experience successfully closing deals against larger, well-known competitors.
  • Exceptional ability to deliver engaging, persuasive demos and proposals to stakeholders at all levels.
  • Fluent in Clay, Hub Spot, and other modern sales enablement tools
  • Experience in the Legaltech industry will be considered an asset.
Why Estateably

Over the next 25 years, more than $60 trillion will be transferred between generations— yet professionals and the families they serve are wholly underserved in their tools to navigate the estate and trust administration process. Estateably was founded to change that.

Here’s why you’ll want to be part of it:

  • Massive market opportunity:
    We re tackling one of the largest wealth transfers in history, in an industry overdue for transformation.
  • Rapid growth and adoption:
    Since launching in 2021, we’ve become the fastest-growing estate and trust platform in North America, serving 1,000+ firms across Canada and the U.S.
  • Real problems, real impact:
    Our platform helps fiduciaries handle complex, sensitive workflows that directly affect professionals and their practices.
  • Bold, ambitious vision:
    We’re not here to make small improvements—we’re rethinking how the industry works from the ground up.
What Our Team Has In Common
  • A hunger to learn fast and continuously.
  • High ownership and accountability for results.
  • A can-do, solution-oriented mindset.
  • Strong collaboration skills and a team-first attitude.
  • Comfort with change and fast-paced environments.
Perks & Benefits
  • Flexible hours & remote work.
  • Yearly bonus based on performance.
  • Full participation in our company’s group health and dental plans.
  • Wellness Benefit.
  • Computer equipment.
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