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CoachAccountable Director of Customer Support and Hand Holding

This past Saturday at about 11:15am I posted a listing for CoachAccountable’s first hire on  Within 48 hours it garnered well over 100 applications, the overwhelming majority of which were incredibly thoughtful and demonstrated serious expertise and ability.

To provide a little behind-the-scenes glimpse into what I’m out to create in the CoachAccountable team, here is exactly what I posted:

About CoachAccountable
CoachAccountable is a platform for coaches to structure and support coaching work done with their clients (think business coaching, fitness programs, life coaching and so on).

It’s going well, and after 4 years my days of doing this as a one-man shop are numbered as business continues to grow.  I’m looking for an independent, sharp and personable individual to join me CA’s first hire and gradually take over the customer support side of things.  Think startup-like freedom but with the stability of an established company.

There are 3 pillars to the position:

I. Fielding Customer Support Issues

Currently relatively low volume, I can usually knock it out in a morning an evening session of 30-45 minutes each. Answering questions, directing attention to how to do this or that, and often pointing out a given article or tutorial video which would answer the specific question but also teach other related goodies. Loads of opportunity to be more awesome by pointing out related things they might be looking for, and thereby educating users further on how to best use the system.

II. Developing the Inline Support Knowledge Base

We’re building an inline help system, a collection of interconnected articles based on various sections and features within the system. Much of the material already exists scattered about in the blog, manuals, etc. It is to be recompiled with updated screen shots, and 2 or 3 versions written for each topic: one as an internal reference for support staff, one for coaches, and one for clients (for client-facing features). There is also much to be written from scratch to flesh out the content to completely represent all the system does (as a one-man shop I indeed haven’t kept things fully up to date!).

III. Customer Hand holding and Concierge Service

SO often folks benefit massively from just being shown around the system, helping them get acquainted with whichever features would serve a giving coaching style or program. CA is wickedly powerful but it takes something for folks to find and realize the benefit of that power, and so often folks left to their own devices just won’t bother, either under utilizing the system or just walking away from it. CoachAccountable is very much in the business of teaching coaches to be better coaches, and someone reaching out proactively to offer that sort of guidance holds great potential to grow the business. It’s the sort of support that bleeds into being a sales role.

Succeeding in this looks like…

Being a clear writer and a patient, personable teacher are key to this.  Being technically sharp and able to quickly learn a software system is nice, but if you’re not a whiz at this sort of thing already it’s fine because you’ll learn and get fluent with how the system works through experience soon enough.

I’m looking for someone who is keen to grow and evolve with this role over the long haul, someone who really learns the system and excels at teaching coaches how to be better and get great value out of the platform will become more and more valuable over time.  Because it’s an early stage company there is a LOT of room to innovate and make yourself massively valuable, while enjoying a wide variety of (hopefully!) intellectually stimulating and satisfying work.  I know what I need today, and together we can co-create your role as we continue to build the team and infrastructure to make a fabulous machine of customer support and on boarding.  Doing webinars and making screen casts for example are two directions in which you might branch out within this role.

Structure of the job

Structurally, the role will begin with an emphasis on you learning the system and easing in to fielding support emails as you learn (i.e. Pillar I above).  Once you get the hang of that you’ll add in Pillar II and begin flexing your copy writing chops to write informative and illustrating articles on how the system works.  Finally once your fluency with the system is comprehensive enough you’ll be able to move on to Pillar III outreach and hand-holding to compliment your other duties.

Hourly contract basis to start, $30/hour.  If you’re awesome and twist my arm I’m willing to consider starting higher.  Again, I view this role as having great potential to grow the business and so the right person, one who’s able to excel from the start and grow over time, is worth a lot.  I imagine the role to commence part time and grow into a full 40 hours a week within a month or two as you get up to speed and are ready to take on more responsibility.  When we’re both clear this is a great fit and love working with each other we can make your position a full time salaried one.

Speaking of loving working together, it is my intention that whomever takes this position LOVES their role, and I’ll do whatever is in my power to make that happen.  I’ll be relating to you as a competent, responsible adult and give you as much freedom as possible (within the needs of the role) to do your thing independently, where and whenever works best for you.  I want this work to be interesting and life giving to you, varied and purposeful from the interactions you have.  For this to work you have to have at least a baseline love for doing customer support, for being a guide over the phone, and for doing writing that teaches.

Application Instructions
In any application here is what I’d like to see:
  • A brief introduction of yourself and your experience with customer support and/or teaching in general
  • Your thoughts on how you would ideally like to spend your time among the 3 pillars of the position and why
  • Answers to these two common support questions, so that I can get a sense for your writing style:
    1. I couldn’t find CoachAccountable in the app store, is there one?
    2. How can I have the system send out a worksheet for my clients to fill out before our sessions together?

To apply: Keen to hop on board as employee number 2 in a successful and growing venture? Great. To be considered for the role, send me an email to In it please include the items listed in the instructions above. Finally please include your own candid assessment of how likely you are to love this role and why. Having whomever takes this role be blissing their brains out as often as possible is one of my top priorities. :)



All told I received a 141 responses to this posting.  I was delighted, honored and humbled by the enthusiasm showed by so many to join the CoachAccountable team, and was saddened by how many fabulous people I simply had to pass on.

I have made my choice and am so excited to have this candidate aboard.  We’re getting up to speed on working together now, and I can’t wait for you to meet him.  Stay tuned!

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