Sid Bolton

Career counselor · Des Moines, IA · virtual

"I help executive and emerging leaders unlock fresh momentum, gain strategic clarity, and step into their next level with confidence and measurable results." (in their words, on their website)

Services

ServiceWhat is includedPrice
Career Clarity Collective - Small Group Coaching
Mid-Career Professionals
6 sessions · 12 weeks · 6 uniquely designed 90-minute sessions over 3 months · Engaged small group capped at 8 participants plus coach · PRO-D Assessment and 1x1 executive debrief with certified coach · Personal Career Rubric calibrated to unique values, passions, and wiring · Executive-level coaching experience without executive-level cost $747
Executive Architecture - Executive Coaching and Advisory
Purpose driven executives
1:1 sessions · Executive advisory · Fractional leadership · Speaking engagements on request
Level Up Coaching - Executive and Business Coaching
Executives, Next-Level Individuals, and Businesses
High-impact coaching uncovering opportunities · Tackling challenges · Accelerating lasting growth on request
Speaker Engagements - Keynotes and Talks Captivating storytelling · Sharp insight · Clear actionable strategies on request
Workshops - Dynamic, Results-Driven Workshops
Businesses ready to level up
Half-day intensives · Full-day deep dives · Two-day transformations · Customized practical frameworks and guidance on request

As published on their website, read Sep 30, 2026.

How they compare

Computed by Callings from the prices and experience coaches publish. Not a rating.

Where they fit

StudentsEarlyMidManagerDirectorVP / C-suite
Resume and LinkedInnononononono
Interviews and offersnononononono
Job search strategynononononono
Career direction and changeyesyesyesyesyesyes
Leadershipnononononono
Personal brandnononononono

How they work

Process
Prospect: Explore true self and desires · Survey: Identify obstacles and resources · Architect: Design opportunities and build toward possibilities
Assessments
PRO-D Assessment
Before coaching
Chief Customer Officer, SaaS and tech; Chief Revenue Officer, SaaS and tech; Chief Operating Officer, SaaS and tech; Integrator, SaaS and tech

Do it yourself, or hire a coach?

Doing it yourselfUsually enough whenA coach earns the fee when
Career directionWeeks of reading and conversations about roles that fit. Callings can show your strengths and the pay for each role.You already have two or three target roles.You do not know what comes next, or you want structure and a formal assessment.

Times are our estimates. Try Callings.

Questions to ask before hiring

  1. If I land a job partway through, what happens to the sessions I have not used? (multi-session package)
  2. What are your cancellation and refund terms? (no refund terms on their site)
  3. Who do you usually work with, and how long does a typical engagement last? (always worth asking)

What they publish

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