About

Jon D.Anderson

Founder and 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

Jon is a builder, a data analyst, and a leader and mentor of revenue operations teams, all in one. He started his career in Silicon Valley. First by coincidence, then on purpose, Jon joined organizations that needed something built or fixed so the sales teams he was part of, and later led and managed, could consistently succeed. So he built or rebuilt what was needed. When the revenue engine was delivering consistent, reliable results, Jon moved on to the next fix.

Today Jon serves as a fractional or interim CRO to founder-led businesses, including technology and professional services firms whose growth has stalled, or still runs through only a few rainmakers. He collaborates with the founder and leadership team rather than handing over a report and leaving.

  • RoleFounder and CRO, The Sidehill Group
  • Works withFounder-led businesses in the technology and professional services sectors
  • ExperienceFounded The Sidehill Group in January 2009
  • IndustriesTechnology, professional services, advanced manufacturing
  • Based inPalm Springs, California

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].

© 2026 The Sidehill Group. All rights reserved.