Love what we're up to on Dean Street? Are you my next Chief of Staff?

Chief of Staff has always been a term I use intentionally -- rather than assistant or business manager -- because I find running a small business very much like running a Presidential campaign or term. One, it's high stakes. Two, it's deeply personal.


On the high stakes end, let's be honest: the fact that I decided to launch a business less than three years ago, with zero training, zero mentors, and made it profitable in under two years with no financial safety net in the most expensive city in the country ... is insane. {wink} I lept.

And I continue to leap. Because now my desire is not just to survive {pay my rent} but thrive {you know, wild things like having health insurance and a retirement fund}. And, to create that lifestyle for a small team -- you! My vision from day one has been that there will eventually be about four of us who are Dean Street Society, full-time, with benefits and all that jazz.

That means the business I built alone, needs to be growing and scaling, which is why your role is so important. This position is about deepening this business for the team as a whole so we can live lives with lots of freedom while working within our skill sets to help others.

A Presidential term is high stakes because you're trying to do incredible things, against all odds, with a ticking time clock. That's the energy I bring to this, and what I look for in my team as well. You never join a campaign just to pay your grocery bill. You join because you believe the vision matters.

It's about passion.


On the personal end, a President's name is always what's on the line.

If AT&T has poor customer service you rail against the company. But does anyone actually know who founded AT&T? Do you think they read the emails? Definitely not. But if a policy goes awry, it's the President's name in the headline. There's not a big business name of anonymity. There's a personal face, which means all the decisions are and feel very personal.

I often compare entrepreneurship to being the single parent of triplets. And in that analogy, you're the Mary Poppins -- the nanny in whom these precious creations are trusted, to be loved like your own. You don't hop on a campaign just because the candidate is a Democrat or Republican {insert: entrepreneur}. You raise your hand because you believe this candidate is going to make a difference.

It's about heart.


Therefore, a Chief of Staff is a rare bird.

They have passion and heart for something they're an integral part of behind the scenes. They have the President's back, and the President has theirs.

They aren't the face of the story, but the story is just as much theirs.


The Story

Here's a glimpse inside my long-term vision for Dean Street Society:

  • In 2015 we'll scale from a 6-figure business to multiple 6-figures and bring on our next full-time employee after you.
  • We'll grow our list and social media followings so we can impact tens of thousands each year helping them to authentically increase their confidence with an educated style, alluring business and inspired life.
  • As a role model for younger girls, and continued inspiration to women in their 70's, we'll do our part to reclaim the lack of self-confidence that comes from our style and beauty, and the exhaustion and fatigue that comes from building unsustainable small businesses.
  • The About page on Dean Street Society will be not just about Hilary, but list our small team of 4-5 full/part-time folks who work together to keep this business growing.


The Daily Dose

My Chief of Staff is responsible for: 

  • Customer service and correspondence. Writing/email is a large part of this position, and being able to strike the right balance between warm and professional while speaking with mentors, brands, colleagues, clients and readers.
  • Systems and organization. Keeping things running smoothly behind the scenes whether that's making sure the bookkeeper is on top of payment plans or email blasts are cued up throughout a program.
  • Teamwork and management. Communicating with members of the team such as our bookkeeper, graphic designer, web designer and videographer on projects. As well as delegating to and overseeing our seasonal interns.
  • Brainstorming and big picture thinking. As my right hand person you're the one I process aloud with, talking strategy, revenue streams, marketing.

The details of this position: 

  • This position is virtual and part-time or full-time, dependent upon circumstances and experience.
  • Hours are flexible, but set/consistent.
  • A part-time position might look like 11-3pm EST Monday through Thursday; full-time might look like 9-5 Monday through Friday. Availability in the late morning or afternoon is required. The position cannot be completed on nights and weekends, as we'll co-work -- texting/emailing/calling throughout your scheduled work hours.
  • Hourly pay is dependent upon experience. You may begin at a lower salary during a training period, with a raise 3 months later.


Your Gifts & Goals

This position is ideal for someone who:

  • Desires to be a part of the entrepreneurial/blogger world, learning about marketing, social media strategy, copywriting, attending conferences and networking events. I want your mind to be blown by how much you've learned and grown two years from now.
  • Gets a rush from strategy and success and story building. You get a kick out of analyzing the data on our Facebook ads and listening to webinars to figure out how to kill it on our conversion rate. You get choked up reading the thank you emails from our delighted customers because you know we've made a difference in their lives.
  • Desires location independence {you can work from anywhere in the world; from your couch or local coffee shop} and flexibility {unless we're in the midst of a big launch, I'm very accommodating about vacations, time off, enjoying and living your life so you can come back refreshed and renewed}.
  • Desires to play in their strengths. I'm very committed to finding out what my team is best at, and letting them use that. If we find an area that's not your strength, we'll make it part of the job description and skill set for the next person we hire, or bring on interns to support you in that. If there's an area you love, let's get you more training so Dean Street Society can benefit even more from your talents and natural aptitude. 
  • Can make a two year commitment. A presidential term needs consistency, in order to keep making progress. A new mother benefits most from Mary Poppins when she can develop trust and know that Mary knows her children as well as she does. 
  • Wants to be the Julie to a Bethenny, the Huck to an Olivia, the Leo to a Bartlett. Julie/Bethenny is the best example of this specific relationship. Julie assisted her at a party before she was "anyone" and said "you're going to be big, and I want to be a part of making that happen". She started to work for Bethenny before she could even pay her, and was an integral part of building a million dollar business, going on to become godmother to Bethenny's daughter and with both in tears when it was time for her to move on. Now I have no plans for a child so you're off the hook for godmother. {wink} Yet that relationship made me cry before I ever thought of becoming an entrepreneur like Bethenny. Sisterhood, partnership, building something, watching it grow, telling marvelous stories -- that's what Dean Street Society is about, and therefore what our team is about.
  • Desires an employer who cares about their story. I've had past employees who were putting their husband through graduate school, knew what month their other part-time job would phase out, wanted a job they could take with them when their partner was transferred, start work when they drop their kids off at school -- it's my desire to help my team craft the lives they want, and for this to be a mutually supportive relationship of where we both want to be in 2-3 years and how Dean Street Society can get us there.

This position is not for you if:

  • You want to be president in the next few years. If you're looking to launch your own business full-time in the next 2-3 years, congratulations! However, this is not the position for you.
  • You're looking for a job in the interim of another goal. It is my explicit desire to hire someone who will be on our team for a minimum of two years.
  • You're looking for a job. Period. Listen, there are easier jobs. So much easier! Punch in, punch out, no one's got their heart in the game so it's pretty easy breezy. If that's the stage you're in, go find those jobs! {Seriously I envy you and wish I could be fulfilled by a simpler life!} This position, is for the girl or guy who's unfulfilled punching the clock at a random desk job that no one really cares about. You know I'm going to call you in tears sometimes, and that's okay. There IS crying in entrepreneurship. Bethenny cries, Olivia panics, Bartlett gets angry. Because when you play with heart, it's harder, but so much more worth it.
  • You have a thin skin. I have a thin skin, I get it! I need someone who can shield me from a lot, take a lot, and deflect a lot of the pressure that lands on me directly. I need the yin to my yang in this area. I'm still losing sleep over negative things said six months from now. I need you to be able to brush it off like I wish I could. {wink}

You have a strong skill set in:

  • Fabulous writing, sweetheart customer service and chic organization a must
  • Knowledge of marketing and the entrepreneurial world a strong plus
  • Business strategy and management are skills you desire to grow in more
  • Squarespace, AWeber, Photoshop and Illustrator knowledge a minor plus


How to Apply:

Are you still with me? Listen, my phone calls are long-winded like this post, so if you're still reading that's a sign you can hang with my musings and tangents. {wink}

Send an email asap to with the subject line "Chief of Staff Application" including:

1. Why the idea of this position makes your heart sing and you're the perfect person for the job. This may include your past work experience if applicable, but you could have been a circus in the clown for a decade and be killer at this job, so a formal resume is not needed.

2. What are your best skills sets. Hey I may not have noted something that you can bring to the table, so sell me on why your talents and idea would bless Dean Street Society.

3. What your current work scenario is. How soon are you available to begin? Do you have another job you would be leaving? A part-time job and if so what are the hours? And what your ideal work scenario would be with Dean Street Society. Are you more interested in part-time or full-time and what hourly rate are you seeking to begin at.

4. Where you'd like to be in 3 years with your life and career.

5. Your reply on behalf of Dean Street Society to the following emails {in truth you'd be given more guidance and insight from me, but this is just to get a feel for your gut instincts and writing style}:

"Hi Hilary. So I've been a fan of Dean St for a longtime. But I'm disappointed by one of your recent Instagrams. Usually you're so classy, which is why I respect you. So why would you post a photo of you in a bikini?! I want style inspiration, which is why I follow you, not to see what you look like in a bathing suit. I get that you were on vacation, but if you really care about supporting women and their self-image like you say, and almost no one is a size 2 like you, then it feels disingenuous for you to be flaunting how thin you are. No need to reply, but just wanted you to know."

"Hi Hilary! I have to confess I'm such a fan! You're doing everything I want to do in life. I'm coming to NYC August 11-13 and wanted to know if I could take you to coffee to pick your brain and get advice on how to start a business like yours? I just want to know how you got started, what you think I should do first -- I'm so excited but have no idea where to begin and know you have all the answers! Can't wait to hear from you."

"Hi team. I'm one of your current students and I have a favor to ask. I was so excited for your program when I signed up, but it turns out I just haven't had the time I thought I was going to in order to participate. I know you have a no refund policy for this class, but will you please make an exception since I'm not actually able to take advantage of it right now? Thanks in advance!"

6. Links to your social media profiles and blog/website, if you have them. Just to give me a feel for who you are!


I'm so honored you'd want to join in this story and adventure, and hope you're the Chief of Staff I've been dreaming of ...