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Helping Hand


Outside Looks is a boutique consulting firm founded by Carrie Watson in 2016.

We help specialty outdoor retailers across North America financially plan and manage their merchandise. 

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Role: Retail Expert

We are looking to fill the role of a 1099 independent contractor, 100% commission.

About Outside Looks:

Outside Looks is a retail consultancy rooted in the outdoor and related retail industries.

Our mission is to provide an objective voice to retailers that guides their merchandise buying. We modernize and ‘profitize’ specialty shops by implementing the same big data tech approach and concepts that the retail giants use. This powerful, predictive intel helps us guide retailers with realistic goal-setting and insightful business mentorship.


Our team is responsibly growing as our long-term client base continues to grow. We’re planning just under $100m of annual revenue for specialty retailers. We're looking for a special person to build their own consulting business as well as manage existing client relationships. We're looking to onboard this person in early 2023 so leadership can focus and expand into additional offerings and revenue streams.

You’re our ideal candidate if…

  • Your co-workers have historically looked to you for knowledge and mentorship.

  • You enjoy maintaining long term relationships.

  • You carry a natural curiosity to understand others and their motivations…and you're slow to make assumptions or opinions of others.

  • You have a natural aptitude for numbers, problem solving, and autonomy.

  • You’re prompt and courteous in meetings and manage your calendar diligently.

  • You enjoy prepping for meetings and discussing your findings over Zoom for the majority of a typical work day.

  • You can handle a few months of low income while building your practice. 

Perks and benefits of joining our team:

  • Work remotely via web meetings, email, phone calls

  • Create and manage your own schedule without PTO limits

  • Occasional travel to clients, tradeshows, and training events

  • Invest in meaningful, lasting relationships with clients

role filled

Job Overview:

Becoming an Outdoor Retail Expert is a remarkable opportunity for the right candidate to build a rewarding consulting practice leveraging Outside Looks’ methodologies and brand recognition among independent outdoor retailers. Outside Looks is a proven provider of Management One’s merchandise planning software and uses a thoughtful educational approach to helping independent retailers.

At Outside Looks, we are looking for a special individual who will help our clients increase revenue and cash flow through improved inventory management. Every month, you will identify potential opportunities and challenges through a quantitative & qualitative analysis based on our merchandise planning reports and open-to-buy management. You will consolidate your findings to develop and present a concise and actionable plan to the client in a motivating manner. You are also responsible for following up and holding the client accountable for following the plan. Ongoing relationships are positive, respectful, and full of important stories of context...unique to each client and buyer. We must consistently deliver value to the client throughout the engagement.

Detailed Responsibilities:

  • Become proficient in the use of proprietary buying tools.

  • Successfully pitch, close, setup, and onboard new clients.

  • Build rapport and credibility with the client by providing value with each interaction.

  • Perform a quantitative analysis of the client’s data and their financials (P&L, Balance Sheet, Breakeven, Cash Flow).

  • Identify patterns and trends in the analyzed data, communicate to the client and present solutions.

  • Meet with the client in person, phone, or video conference (typically 1-2x a month per buyer).

  • Provide client training on our platform to maximize the client’s knowledge and use of the reports and tools available.

  • Motivate the client to make change and stress the benefits they will experience. Hold the client accountable on agreed action items; guide and coach them to achieve set goals…ultimately focused on improved retail performance.

  • Attend and graduate from our preferred merchandise planning training program. This is a remote program with weekly evening lessons and occasional group work. Approx 2-3 months of learnings scheduled for early 2023.

  • Ability to travel:

    • To newly acquired clients and/or upon client request.

    • Travel (tentatively scheduled for March) to wrap up remote certification training program.

    • Trade show attendance is required at Grassroots Connect (June 12-15, 2023 in Knoxville, TN. November 6-9, 2023 in Kansas City, MO)


  • Professional retail background required. Retail buying in the Outdoor vertical is a plus.

  • Bachelor’s Degree or higher strongly preferred.

  • 5+ years' experience in the retail sector - retailer, wholesaler or vendor to retailers - including at least a basic understanding of retail business models and retail math.

  • Strong quantitative and qualitative analysis skills.

  • At least basic financial analysis skills are strongly preferred.

  • Strong critical thinking and problem-solving skills - analytical, innovative & creative.

  • High degree of emotional intelligence & confidence to deal with a diverse portfolio of clients.

  • Exceptional written, verbal and presentation skills.

  • Excellent listening skills with the ability to ask the right questions.

  • Ability to embrace new concepts and implement them.

  • Proficient in using spreadsheets and basic understanding of Point of Sale software.

  • Ability to be self-directed but also a contributor to a team.

  • Embrace and embody our purpose.

Interested? Email with a short intro and your resume.

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