Building Your Retail Dream Team: Your First Hire
How and who to find as your first hire building out your retail channel
The tl;dr
Building a new channel is like building an entirely new business; your first hire is essentially a mini CEO
The ideal candidate depends on which tradeoffs you’re willing to make more than others
Interview questions should touch on their past experience, and give you a glimpse into how they build new things and tackle problems with limited information
The channel’s first hire can’t be successful if they’re not given the proper onboarding; leverage playbooks, dashboards, and SOPs from existing channels and build from there
Just as the channel will evolve and grow, so too should this new leader; invest in their knowledge and broaden their experiences in ways that are complementary to their current skills
The importance of the first hire
In the ever-evolving landscape of retail, direct-to-consumer (DTC) brands face a unique challenge: how to successfully branch out into the retail space. The key to this transition? Your first hire. This isn't just any hire; it's someone who's climbed the ladder from a General Manager in stores to a role in retail operations at a corporate level. As you build out the channel for the first time, you’ll need someone who understands “how the sausage is made” at the store level, and how to balance store teams’ needs with corporate level budgets.
This newsletter will guide you through finding, interviewing, training, grooming, and leveling up this pivotal team member.
Identifying the ideal candidate
Imagine a candidate who has not only managed the day-to-day operations of a retail store but also understands the bigger picture of corporate retail operations. This blend of ground-level management and strategic oversight is what you're looking for. These individuals bring a wealth of knowledge in customer service, operational efficiency, and team leadership.
But where do you find them? My general recommendation is to look for candidates whose LinkedIn resumes show recent progression from store level General Manager to District or Regional Manager. Even better if they were moved into a Retail Operations role. I say recent progression because this person will need to be in the weeds, often acting as the GM for a short period of time — and Regional/District Manager veterans will likely not be interested in a role that requires them to step back into the weeds, while recently promoted folks may be willing to get their hands dirty for a short while if there’s upward career trajectories should they succeed (ie a path to “Head of Retail” in the not-so-distant future).
Here are a few examples of LinkedIn profiles I like, modeled after real people I know who succeeded:
Profile 1: Previously GM at a startup retail brand, where their experience spanned multiple locations and showed clear progression to eventually running the flagship location.
2018 and beyond: Director of Stores (was hired out of the gates as the Director)
2014-2018: Store Manager (within 1 brand, but who was at 3 different locations across this time period; the last location was the flagship)
2007-2014: Retail Salesperson —> Assistant Department Manager
Profile 2: Began career in the field as a Store Manager, then moved into Operations with clear progression to leadership.
2014-2020: Director of Store Operations (at a couple different brands)
2010-2014: Store Operations Manager
2008-2010: Store Manager
You can either scour LinkedIn, or leverage one/both of the Job Descriptions from the 1REC resource hub:
The interview process
Once you have candidates lined up, it's time to dive deep into their experiences and see how they operate under pressure. Your interview should be a mix of understanding their practical skills and gauging their fit within your brand's culture, including managing through inevitable growing pains.
Ask questions that reveal their approach to challenges they've faced in retail settings, their adaptability to change, and their vision for a retail channel within a DTC brand. Remember, you're not just hiring for what they've done, but for what they can do for your brand. Here are some example interview questions:
Can you describe a challenging situation you faced while managing a retail store and how you resolved it?
This question aims to understand their problem-solving skills and ability to handle retail-specific challenges.
How have you adapted store operations to align with corporate strategies in your previous roles?
This question assesses their ability to translate broader corporate strategies into actionable plans at the store level.
What strategies have you implemented in the past to improve customer experience in a retail setting?
This question is designed to gauge their understanding and prioritization of customer experience in a retail environment.
Can you share an experience where you had to train and develop a retail team? What approach did you take?
This question evaluates their leadership and training skills, crucial for the role.
How do you see the retail channel changing as the brand goes from zero to 1 store, and then from 1 to 10, and 10 to 50?
This question assesses their foresight and flexibility as the channel grows, and processes and expectations inevitably grow with it.
Describe a time when you had to implement a significant change in a retail operation. How did you manage the transition?
This question looks for their change management skills and ability to navigate through transitions smoothly.
In your view, what are the key differences between managing a traditional retail store and a DTC brand's retail operation?
This question tests their understanding of the nuances between traditional retail and DTC retail operations.
How would you approach setting up a DTC brand’s first location?
This question seeks to understand their strategic planning skills and ability to conceptualize and execute new initiatives.
Can you give an example of how you've used data to make a decision in a retail context?
This question is aimed at understanding their data-driven decision-making skills.
What’s your 30, 60, and 90 day plan?
This question assesses their ability to articulate a plan in the absence of relevant information (such as your timeline, budget, etc.). In the beginning of the channel’s lifetime, they will be operating as the sole channel expert and with limited information or guidance, so this question helps to see how they think accordingly.
Training and onboarding
Bringing your new hire into the fold of your DTC brand is a critical step. They need to understand your brand's ethos, your customer base, and your existing operations.
Develop a comprehensive onboarding program (or literally just a document) that covers the following areas to set up for success:
1. Key cross functional partners: as the first hire of the retail channel, this new role is effectively a new CEO within the business. They need to spin up everything from HR to budgets, operations, and even reporting standards and best practices. Assuming you’re a startup with a lean organizational structure, they should meet with each Director in the company (ideally there are 10 or less of them) in order to establish direct contact with each area leader.
2. Existing new hire onboarding: In many cases, your company has an existing onboarding process, including presentation materials, benefits overviews, etc. Share or review this process with this new hire so they can understand where it might need to be augmented with store-specific subject matter. This role will be spearheading one of the most crucial elements of the channel: recruiting and training for store staff.
3. KPIs and reporting: This role will need an understanding of your brand’s existing reporting and KPIs, so they can emulate the same standards and metrics for the new channel. If they have visibility into your existing e-commerce and/or wholesale metrics, these will act as good benchmarks as they assess the new retail channel’s performance.
4. Budgets: Chances are that your finance team has put together some form of a budget for the channel that illustrates the expectations for sales, and the budget for operating expenses across 4-wall expenses, vendors, and salaries. This should be shared with them immediately so that they have full transparency into what they and the new channel are expected to deliver.
5. Strategy decks and analyses: By the time you’ve made this hire, you’ll hopefully have had a robust discussion with your executive team, board, and others. Which means there are probably some presentations and analyses floating around that include everything from rollout plan, competitors and peers, budgets, and even moodboards / renderings / examples of store concepts you’ve all collectively decided to replicate in some form. These would be helpful for the new hire to get up to speed.
6. Vendor introductions: If you engaged any consultants or relevant vendors before making this hire, they should be introduced to this person so they can get a sense for who’s doing what.
7. Folder drives: This sounds trivial but is often overlooked, and should be straightforward.
Leveling up
As your first hire becomes more comfortable and proficient in their role, start looking at expanding their responsibilities. This could mean giving them a more significant role in strategic planning or preparing them to manage a larger team as your retail presence grows. Their growth should align with the expansion of your footprint, making them a cornerstone of this new channel.
In order to get there, you may need to invest in training or coaching to help them get more well-rounded. Depending on the profile of your first hire, it may be easiest to level them up in certain areas over others, so I’ve listed a few thoughts below on how this role may progress based on my experience managing folks of various starting backgrounds:
Retail Operations: these roles have likely spent a lot of time working with Retail Leadership (GMs, DMs, RMs; or Head of Retail / Real Estate / Finance / CX). Instead of pushing them to learn a completely new subject matter with a steep learning curve (eg real estate or construction), give them more training in and purview of Retail Leadership by exposing them to more strategy and KPIs to manage.
Retail Leadership (GMs / RMs / DMs): these roles typically have great people skills and have seen the end results of corporate decisions. They likely have strong familiarity with Corporate Operations, but haven’t had as much of a peek behind the curtain to see how or why some decisions get made the way they do. Pull them forward in the decision making timelines in Operations and/or Finance so they can be a part of the discussions on how to achieve sales goals that they inevitably have to execute.
Real Estate: these roles are typically rooted in deal making and running a process to procure new leases. This means they’re great PMs, and know how to pull in stakeholders at various parts of the process. They usually also work hand in hand with Construction team members or vendors. The easiest functional area for them to learn is naturally Construction, but they can usually also take on Retail Operations or lean more into spreadsheets with Finance.
Construction: these roles are experts at managing timelines, projects, and budgets. They often take on some elements of Retail Operations vis a vis Facilities & Maintenance, so it should come as no surprise that they are a natural fit to take on more of the Operations responsibilities. Because they also work hand in hand with Real Estate on a regular basis, it could also make sense for them to lean more into managing Real Estate directly.
Strategy / Finance: these folks are great with numbers and thinking ahead, and often have the same technical skills as those doing Real Estate. They think in numbers first and foremost, and manage vendors to some capacity. As a result, I’ve found folks with this background are best suited to slowly take on Real Estate if they’re looking to get more involved with the channel.
(More on how I think of the channel’s functional areas here.)
Some additional, final thoughts
Your first hire in building out a retail channel is more than just an employee; they're the bridge between your DTC operations and your retail aspirations. The process of finding, training, and growing with this individual requires patience, strategic planning, and a keen eye for potential.
You’ll rarely find the perfect candidate, so you should focus most on where your needs are, whether to outsource or hire for it, and at least have a sense for where your resulting blind spots are. Mistakes are inevitable, but having the right first hire can at least help you know where those mistakes will likely come from.