Rob Sullivan
Career Coach
Getting Your Foot in the Door 
When You Don't Have a Leg to Stand On

(McGraw Hill)

For general information about how to find and hire a career coach, read Rob's free online guide 11 Questions To Consider Before Hiring A Career Coach

Rob Sullivan has been instrumental in my career development, playing a key role in two successful job moves over the past 3 years. From re-working my resume and how I viewed my strengths to coaching me on interviewing and job offer negotiations, his help has been invaluable. Rob was able organize and craft my complicated background into a compelling story via my resume. I got more responses from my new resume in the first 3 weeks than I had in the prior 6 months with my old resume. Three recent interviewers specifically commented on how much they liked my resume and how well it answered all of their questions. One recruiter said that mine was his favorite resume and asked if he could use it as an example when working with other clients. He has also helped me to conduct my salary negotiations in a straightforward and open manner that didn’t paint me into a corner. I point all of my friends in the job market to Rob and he holds my highest recommendation.

--John Marcos 

Hiring Rob Sullivan as Your Career Coach

Who would benefit? What industries and positions?

Where and when does the coaching take place?
Why hire Rob?
Tax benefits of hiring a career coach
About Rob
Rob's Availability

would benefit? What industries and positions?

  • Are you having trouble figuring out what's next? 
  • Do you feel your search has stalled? 
  • Have you sent résumés for jobs that appear to be tailor-made for you and received no response? 
  • Are you thinking about changing careers completely? 

If you answered "yes" to even one question above, let's talk. I'm confident I can help. Whether you need resume and cover letter help, interview coaching, networking assistance, negotiation strategies, or a combination, I'd be happy to tailor a program to fit your individual needs. 

To date, I have helped people in positions ranging from entry-level to company presidents in careers ranging from accounting to microbiology. Here's a partial list of the types of careers I've worked with: 

Accountants  Administrative Assistants Advertising Executives
Attorneys/Paralegals Consultants Computer Programmers
Copywriters Developers (Computer) Direct Marketers
Event Planners Fashion Designers Graphic Designers
IT Professionals 
(wide range)
Microbiologists Office Managers
Options/Futures Traders Payroll Clerks Project Management & Project Management Office
Sales Reps Sales Promotion Execs Secretaries & Receptionists
Travel Agents Warehouse/Distribution Web Designers & Developers

does the coaching take place?
I am available for coaching in person and over the phone (with additional support via email). We can meet at any mutually convenient place. While it's always helpful to meet face-to-face, it's not critical. I've coached a number of people successfully over the phone without ever having met them in person. 

Most coaching sessions occur during normal working hours. However, for people who are currently employed and unable to meet during the day, evening or weekend sessions are an option.   

Rob’s methods and advice were valuable and effective during every phase of my job search process: from self-evaluation to job research to getting in the door, interviewing and landing the job. Rob helped me focus my strengths and clearly communicate them to potential employers. With his help, I was able to meet my goals of finding a good-fitting job in the targeted field.


Ken Powers

Chicago, IL


Rob, I just wanted you to know your interviewing and negotiating advice was stellar. Believe it or not, I was totally relaxed on the way to the interview. I just kept thinking - I'm the best one for this job! Plus I made sure I asked the "right" questions. I made it known exactly why I was a good candidate and what I could add to the project. 

After 3 months on the job, using a lot of your sage advice, I requested and got a 50% raise. It works!

Nancy H. 
Wheaton, IL

"As a recent graduate from Northwestern University, I knew I carried the school name but found myself stumbling for words during interviews.  What made things worse (and ironic) was the fact that I was a communications major interviewing for investment banking positions. But that's where Rob came in. A few minutes into the conversation, Rob presented in a clear fashion several major obstacles current grads like myself go through when getting interviewed and gave key advice on how to overcome them.  Example: one of my major challenges was learning how to tell a concise yet meaningful story on how and why I changed course to pursue a career in finance.  Although my fellow classmates recommended reading books like the Vault Guide to Investment Banking and WetFeet I-Banking Interview Practice -- which I did -- it was only after speaking with Rob (he's been through countless situations like this) that I truly felt confident in my ability to stand out amongst the competition and land that highly coveted position.  Within the course of a couple months, I landed several interviews, flew out to several cities, and recently accepted a great offer at a premier investment bank.  I am a success story because of Rob, and I highly recommend -- and commend -- his passion to see recent graduates reach their full potential."

Chris Hwang 
Hanover Park, IL

Why hire Rob?
I could go on and on about how and why my coaching is effective, but it's more believable to hear from my clients. If the information above didn't convince you, read the email from Mak Datar below.

From: "Mak Datar"
To: [email protected]
Subject: Update
Hello Rob,

I am writing to give you an update on my job search process. It is over!

I started my new job last week as a Senior Associate at a global hi-tech 
consulting firm.  It is as close to my dream job as reality will allow! 
Perhaps a dream job is just that -a dream - perfect in its unattained and 
unattainable state?  That said, my new job has so far exceeded most 
of my expectations!  It is now time for me to get to work.

Rob, I want you to know that you have been integral to my job search 
process - as counsel and inspiration.  The tools and techniques that you shared 
with me were very useful and helped bring structure and focus to my daily 
routine.  Your review and feedback of my resume and cover letter led me 
through self-reflection and helped me develop a better sense of where I 
had been, where I was, and where I wanted to go - essentially helped me 
position my marketing message.  Most importantly, you encouraged me to dream 
big, and to transition from the momentum of mediocre reality into the realm of 
possibility.  Our conversations and your advice inspired me to trust my instincts.

You may not realize the impact of your guidance - it has been invaluable!  
I really appreciate all your help.  To express my appreciation for your 
counsel, and to share with you the interesting story of my job search 
process, I would like to invite you to lunch.

I am heading to Melbourne, Australia in a week or so for my first 
project.  If possible, I would like to meet with you for lunch before I leave. 
I hope you are doing well.  I look forward to hearing from you.

Best regards,
Mak Datar


Tax Benefits of Hiring a Career Coach
Job hunting expenses are typically DEDUCTIBLE on your income tax returns. As such, my services are typically fully deductible. But check with your accountant for specifics because I'm not a tax professional and laws in your area may differ. 

Best regards,

Rob Sullivan


About Rob
Rob Sullivan is a Chicago-based career coach, inspirational speaker and corporate trainer whose passion is helping people recognize, leverage, and communicate the gold in their backgrounds.

Rob started his career at Leo Burnett after enduring an ego-battering 80 advertising interviewers over a 12-month period. Twenty-three of those interviews were at Burnett, a company that rejected him when he first applied.  

In addition to his role in Client Service, Rob volunteered as a Burnett recruiter and interviewer. He also began coaching the many friends and strangers who were inspired by his ability to convince Burnett to hire him after the previous rejection.  These experiences led Rob to write Getting Your Foot in the Door When You Don’t Have a Leg to Stand On (McGraw-Hill), a book that has already begun to replace top-selling What Color is Your Parachute? as a text in career development courses. Rob is also the author of numerous eBooks designed to help people in transition. 

Over the past 19 years, Rob has coached people at all levels across a wide range of industries and careers including, but not limited to: CEOs, CFOs, CMOs, COOs, Hollywood script supervisors and assistant directors, financial service professionals, engineers, consultants, IT professionals, options/futures traders, event planners, talent/booking agents, software designers, graphic designers, fashion designers, advertising and PR professionals, and microbiologists.

Like many career coaches, Rob works with clients on issues ranging from career selection, résumé and cover letter writing, mock interviewing, networking, and negotiation. Unlike most career coaches, Rob is particularly adept at helping career changers. By constantly challenging the limiting beliefs and helping people understand and explain why a particular career is the Next Logical Step, Rob has helping many people transition to completely different careers. His successes include:

  • Repositioning a concert violinist who played with The Chicago Symphony Orchestra, The Moody Blues, and Chicago for a career in advertising account management at Leo Burnett, a company that rejected her a few months before.

  • Helping a seasoned software and training professional secure a full-time position designing toys.

To date, Rob has delivered 3 commencement speeches and been a repeat guest on television and radio stations across the country including NBC, ABC, CLTV, WGN, and The Stock Market Observer.  He was also featured in the Wall Street Journal and as a guest expert on Starting Over, a reality show that airs nationally on NBC.

Rob has a BA in psychology from the College of the Holy Cross in Worcester, Massachusetts, as well as an MS in advertising from Northwestern University’s Medill School of Journalism.


Rob's Availability
In addition to in-person meetings, Rob coaches clients by phone and by Skype.

With his ongoing speaking and writing commitments, Rob is only able to accommodate 5 new coaching clients per month. If you are interested in one of these slots, please send an email to Rob (rob at careercraftsman dot com) or call 312-543-8242 to set up an appointment.


To sign up for coaching or to buy Rob's eBooks, please visit: