About

Jon D. Anderson

Founder and Fractional CRO, The Sidehill Group

Jon works with founder-led companies on the gap between the plan leadership believes in and what the team actually does every day. He founded Sidehill to build the revenue strategy, structure, execution, and leadership foundations that make growth faster and more consistent.

JDA

How Jon thinks about revenue

Revenue is a behavioral problem, not a process problem.

Diagnose before prescribing

Every engagement starts with conversations with leadership and the frontline, and an honest read of the revenue data. The fix follows from what that finds, not from a template.

Symptoms aren’t causes

Missed targets, churn, and teams blaming each other sit on a behavior. Every behavior sits on a belief or an incentive. That’s the only level where anything changes.

One system, not three playbooks

Marketing, sales, and customer success are one customer journey. Run them as separate functions chasing separate numbers and lead quality, close rates, and retention all suffer.

Leaders join systems, not rescues

A revenue leader hired to save a broken system inherits the break. Build the system first, then hire someone to run it.

Background

Before Sidehill

[Two or three sentences on Jon’s career before Sidehill: the revenue roles he’s held, the kinds of companies, and what he saw repeatedly that led him to this approach.]

Today Jon serves as a fractional CRO to founder-led businesses, including professional services firms whose growth still runs through a few rainmakers. He works alongside the founder and leadership team rather than handing over a report and leaving.

  • RoleFounder and Fractional CRO, The Sidehill Group
  • Works withFounder-led businesses and professional services firms
  • Experience[e.g. 20+ years in B2B revenue leadership]
  • Industries[e.g. professional services, SaaS, manufacturing]
  • Based in[city, state]

Working with Jon

Two ways to use Jon’s method

Jon built the course so founders can do this work themselves without hiring a consultant. For companies that want him in the room, he takes on a small number of fractional engagements.

Run it yourself

Revenue Is a Behavior

Jon’s full method as a self-paced course: the assessment, the goal foundation, the connected journey, the measurement, and the execution rhythm he uses with clients. Eight modules, 37 lessons.

Explore the course

Bring Jon in

Fractional CRO

Jon leads the diagnosis and the rebuild inside your business, working alongside your leadership team until the system runs without him.

Talk to Jon

Start a conversation with Jon

Tell Jon where revenue is stalling and what you’ve already tried. He’ll give you a straight answer on what’s underneath it, and whether the course is enough. Email [email protected].

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