Meet Sheilah Crowley: Guiding Aspiring Entrepeneurs

We had the pleasure of getting to know Sheilah Crowley, founder and CEO of The Summit, a women owned business designed to create expedient, breakthrough results. Sheilah specializes in working with aspiring and current entrepreneurs to move from stuck and unclear to a place of authority around where she’s going and why, in record time. Sheilah holds a B.A. in Anthropology is also a certified Myers Briggs practitioner bringing insights on the influence of personality preferences in day-to-day decision-making. 

Sheilah Crowley, Founder & CEO of The Summit

VT: Tell me about yourself 
SC: I am a serial optimist, entrepreneur and champion of women. I’ve played several leadership roles both as a professional and as a mother and enjoy coaching and mentoring other women who want to achieve the same – on their terms. I have two amazing kids and a husband who is a real partner when it comes to juggling career and family.
VT:  What lead you to found the Summit Inc.?
SC: At a personal crossroads myself, I founded The Summit based on what I saw as a real need to catch women in transition and provide a platform for using an asset-based approach to repurposing themselves. As women we are exceptionally good at finding and focusing on our deficits or what we don’t know or do well enough. I wanted to change that paradigm.
VT: What is a common trait that you find in entrepreneurs? Anything specific to female entrepreneurs?
SC: A common trait I find in entrepreneurs is an unwavering determination to succeed. The chase is as rewarding as the reward. Women are no different except that I find that women entrepreneurs are more inclined to seek out regular contact with other women entrepreneurs which speaks to a desire for access to support, an openness to problem-solving based on someone else's experience and a natural willingness to share resources.
VT:  Our talent community is made up of women in transition - either re-entering the workforce after a career break or looking to make a change in their current employment path - what is the first step to evaluate whether entrepreneurship is a viable route for them?
SC: One thing I’ve noticed consistently is that while many clients have a great idea for a small business, their ability to succeed is more reliant on themselves as leaders. So prior to even doing the competitive landscape research for the product or service she may have in mind, I would recommend a self-assessment around the entrepreneurial personality and lifestyle. For example, is she someone who exercises extraordinary discipline - staying focused (despite hundreds of tempting business related distractions) - keeping the end in mind at all times? Does she exhibit unwavering determination in the face of multiple challenges and sometimes unreasonable deadlines? Is she able to take in and process new information (that she may or may not like) and pivot in a timely way accordingly? Is she a people person - able to attract talent and customers alike? Is she willing to take calculated risks and bounce back from rejection.
Entrepreneurs can always backfill areas of expertise where they may not have the skills (IT, marketing, administration, etc.), but it is difficult to create a personality trait that isn’t there.
VT:  Can you share a success story of someone who transitioned back to work via entrepreneurship?
SC: We had a client who, prior to taking time out to take care of her family full time, was a graphic designer. When kids got older and she had more time to focus on her interests, she was living in a suburb of New York City and decided to start a business that was focused on design thinking. She learned to think bigger for herself. Instead of settling for designing business cards, she is marketing herself as an art director focused on overall branding.
VT:  What has been your greatest career challenge to date & how did you overcome it?
SC:  My greatest career challenge to date was re-entering after a four-year break. (I wish that there were a Vermillion or Summit available then!). I mistakenly neglected to keep up with my network but luckily I was hired back by my former employer, City Harvest, as an interim program director for a new initiative that I eventually got hired to run. 
VT: Do you have a #FemaleRoleModel? Why are they important?
SC:  My sister Katherine is one of my role models. She is an extremely hard working, funny, accessible and a brilliant psychotherapist. Her depth of knowledge, therapeutic practices and ability to connect genuinely with people is awe-inspiring. She is on my board of advisors.
Women role models that I don’t know personally include, Adele, Meryl Streep and Gloria Steinem.
VT: Is entrepreneurship for everyone? How do you know if you are cut out for it?
SC: While entrepreneurship can be one of the most exciting and rewarding experiences during a lifetime of career choices, I don’t think it’s for everyone. If you think you have a great idea I would try and test the product or service on a very small scale. See if you can write the skeleton of a business plan (at a minimum financial projections and a sales and marketing plan), practice selling the product or service over six months. See if it feels like a fit.
I would also say that entrepreneurship is not for people who really need affiliation – a place to go and plug in with people, projects and outcomes on a daily basis.
VT:  We find many women with great ideas.  Any tips on how to move things along - to go from idea to execution? 
SC: I would recommend these three activities:
  • Write a vision statement by starting with the end in mind.  What do you want to achieve? Research like companies that you imagine for yourself. Microsoft’s vision, for example: Our mission and values are to help people and businesses throughout the world realize their full potential.
  • Second, I would think through what’s going to be your differential. If you want to start an interior design business and you're in a room with five other interior design business owners, what unique perspective do you bring to the table? Fill in the phrase “unlike my competition I ____.” (And by the way, the answer is not just hard working!).
  • Third, I would sketch out a baseline one-year sales plan. How many interior design jobs with how many customers, in which months, at what price point do I need to execute in a year to earn your goal revenue number? See if the math works. Written goals have proven to ensure 10 times the average earned income over companies without written goals (Forbes, 2014)
 VT: What quality is a "must have" as a female entrepreneur? 
SC: The ability to understand what she should do over what she should delegate. Women tend to want to do it all and with that experience high rates of burnout.
VT:  What is the best advice you have received in building a business?
SC: Don’t try to sell your product or service to everyone. Get as specific as you can about who your target audience is, where they get intel, where they shop and how they make purchasing decisions. In doing so, it will help you focus your marketing and sales efforts.
When I started The Summit, I thought that any woman in transition would benefit from what we had to offer. While that may be true, I was deeply scattered (and exhausted) in my first few months trying to reach recent graduates to early baby boomer retirees. Fortunately, after clarifying the demographic and psychographics of my audience I realized my passion to help women, who like me, took time out to be with their children find and repurpose themselves.
VT:  What is a common misconception about choosing entrepreneurship as a career path.
SC: I think the most common misconception about entrepreneurship is that it’s all about the product or service you are offering. If fact it’s more about working on the business - planning, talent and finances.