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The Scalable

Business Advisor - Helping Entrepreneurial Companies Grow & Scale

Full-TimeUpdated on 10/23/2026
$70k - $85k+ Performance-based compensation + HSA company matching + 401(k) company matching
Senior
Remote in USA+1 moreMore locations: Remote in Canada
RemoteUnited States (remote) / Canada (remote): Must be based in a U.S. or Canadian time zone.
ConsultingStrategy & Management Consulting

About the job

Requirements
  • At least 5 years of experience running, scaling, leading, or advising entrepreneurial businesses.
  • Strong communication and facilitation skills, especially in virtual one-on-one settings.
  • Familiarity with business operating systems such as Scalable OS, EOS, Scaling Up, OKRs, or similar systems.
  • Must be based in a U.S. or Canadian time zone and available during standard business hours.
  • Comfort using CRM software, Slack, and Zoom; HubSpot is preferred.
Responsibilities
  • Work one-on-one with a portfolio of 75–90 founders, CEOs, and executives, helping them apply Scalable’s frameworks to solve operational bottlenecks.
  • Facilitate bi-weekly implementation sessions, customizing and installing the Scalable Operating System into clients’ companies during the 16-week Get Scalable Accelerator.
  • Lead quarterly 90-Day Planning Sessions with clients, helping them identify priorities and use tools, resources, and community to achieve their goals.
  • Use questions, tools, and proven models to help clients gain clarity, make decisions, and get results.
  • Drive results through structured accountability by following up, checking in, and encouraging clients to stay on track.
  • Track client progress and sentiment in HubSpot, escalating risks and celebrating wins.
  • Collaborate with Client Success and Program Leadership to ensure a seamless, high-touch client experience.
Desired Qualifications
  • Experience facilitating structured programs or planning sessions.
  • Prior experience in high-ticket coaching, advisory, or mastermind programs.
  • Familiarity with multiple business types and models.

About the company

Company Size

N/A

Company Stage

N/A

Total Funding

N/A

Headquarters

N/A

Founded

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Simplify Jobs

Simplify's Take

What believers are saying

  • The website was updated August 25, 2026, signaling active positioning and sales motion.
  • Recent podcast promotion around hiring CEOs shows continued content-led customer acquisition.
  • Founder-led companies still need operating systems, and The Scalable Company sells that painkiller.

What critics are saying

  • Ryan Deiss admitted The Scalable Company almost failed, signaling fragile demand and execution.
  • The business depends heavily on Deiss's personal brand and DigitalMarketer distribution.
  • Consulting-style offerings face copycat pressure from EOS, fractional operators, and agencies.

What makes The Scalable unique

  • Scalable OS standardizes founder-led companies from $2M-$20M into self-managing businesses.
  • Ryan Deiss brings DigitalMarketer, Traffic & Conversion Summit, and a built-in audience.
  • Founder Fadeout pairs systems, dashboards, and team structure with explicit exit optionality.

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Benefits

  • Health Insurance
  • Dental Insurance
  • Vision Insurance
  • Health Savings Account/Flexible Spending Account
  • Life Insurance
  • Disability Insurance
  • Unlimited Paid Time Off
  • 401(k) Retirement Plan
  • 401(k) Company Match
  • Parental Leave
  • Remote Work Options