Doug Bennett

Career coach · Tampa, FL · in person and virtual

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"More than any other factor, executive talent and leadership are what make or break an organization." (in their words, on their website)

Services

ServiceWhat is includedPrice
Leadership Coaching
Executives who want to build and maintain high-performing teams, and entrepreneurs who wish to start scaling their organization		 build, evaluate, and maintain high-performing teams · optimize output on request
Executive Coaching
Executives		 setting vision and strategy · identifying and developing talent · establishing a pattern of accountability on request
Career Coaching
Those looking to transition to the next level and become an executive, and aspiring executives in earlier stages of their careers		 provide an outside lens to focus efforts where they will have the most impact · equip to evaluate and modify own trajectory on request
Interview Coaching for Candidates
Candidates with upcoming interviews or who desire practice		 tailored coaching · resume critiques included on request
Interview Training for Employers
Employers		 interview training · ensure appropriate matches are made · directly interview candidates on behalf of employers · provide detailed feedback on request
Speaking Engagements
Audiences ranging from intimate groups to 1,000+		 industry-specific insight · data-driven transformations · developing high-performing teams · tailored inspiring and engaging presentations on request
Interim Management
Organizations needing short- to mid-term executive or data transformation roles		 fill executive or data transformation roles on contract basis · help find someone for such roles on request
Department Creation
Organizations establishing new departments		 establish and develop new teams or departments · accelerate new department creation · ensure department is on right course on request
Strategy Consulting
Organizations		 set appropriate and ambitious goals · identify and select from multiple strategies · commit to specific tactics · gain new perspective and capabilities · ensure right organizational structures and talent are in place on request
Operations Consulting
Organizations		 identify waste and gaps in current processes · improve processes in supply chains, sales, software development · focus on opportunity costs · minimize pain of change · work with affected areas to address drawbacks to change on request

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

Where they fit

StudentsEarlyMidManagerDirectorVP / C-suite
Resume and LinkedInnononononono
Interviews and offersnonoyesyesyesyes
Job search strategynonoyesyesyesyes
Career direction and changenonoyesyesyesyes
Leadershipnonoyesyesyesyes
Personal brandnononononono

How they work

Before coaching
VP positions, Data, Analytics, and Sales Operations (5 years); Financial Planning and Analysis, Fortune 500 retailer

Do it yourself, or hire a coach?

Doing it yourselfUsually enough whenA coach earns the fee when
Interviews3 to 6 hours of practice out loud per interview process. Callings can prepare you for each job you track.Early rounds in a format you know.Final rounds, panels, a new kind of role, or you tend to freeze.
Job searchA target list, a weekly plan and steady outreach. Callings builds the weekly plan and tracks every application, free.Interviews are coming in.Three months without traction, or a senior search that runs on your network.
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. What does it cost in total, and what is included? (no published price)
  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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