Stylist

Head of Sales Midnight Oil

Reports To: CEO Location: Remote, with travel as needed Type: Full-time

About Midnight Oil

Midnight Oil is redefining professional womenswear. We design semi-custom blazers, trousers, coats, blouses, and tuxedos, made-to-order, personally fitted, and crafted by European and American artisans to last. Our stylists work with women one-on-one, in person and virtually, across the country.

Our stylist network is the heart of this business. We're hiring a Head of Sales to build it, lead it, and make it exceptional.

The Role

You will own revenue at Midnight Oil, and the stylist network is how we get there.

Build and nurture the stylist network, this is the job. Recruit and onboard stylists in the right markets. Train them to sell consultatively and fit expertly. Coach them individually and hold a consistent rhythm of connection so a distributed team feels like a team. Raise productivity across the network and keep your best people for years, not seasons. Everything else follows from this.

Grow the B2B Business. Corporate gifting, team uniforms, executive onboarding, and incentive rewards are a meaningful secondary growth lever. You'll own the offer and the pipeline, close corporate accounts, and equip stylists to surface opportunities in their own markets. This is a high-ownership role with real upside and room to shape how we sell.

Key Responsibilities

Stylist Network Leadership & Development

• Recruit, onboard, and ramp new stylists; identify the markets where added coverage produces the most return
• Train the network on product, fit, and consultative selling, and keep that training current as collections evolve
• Coach individually. Run a consistent operating rhythm of one-on-ones, market visits, and in-person time so a distributed team stays connected to the brand and to each other
• Own stylist productivity: appointment volume, appointment-to-sale conversion, average order value, reorder rate, and event yield
• Build the culture, recognition, and peer-learning structures that make top stylists want to stay and grow here
• Design commission and incentive models that reward the right behavior
• Manage performance honestly, develop who can grow, and address who can't
• Give the network the tools, collateral, and support that let stylists spend their time selling

Sales Strategy & Revenue Ownership

• Own the company revenue plan across stylist-led, DTC, and corporate channels; set targets, forecast, and report to the CEO
• Identify and execute new opportunities for events, market expansion, and network growth
• Propose incentives that align stylist success with company growth

B2B & Corporate Partnerships, secondary growth channel

• Own and evolve the B2B offer: ideal customer profile, bulk and program pricing, contract terms, and fulfillment
• Drive prospecting and close corporate accounts across target verticals — financial and professional services, law, consulting, healthcare, and executive teams
• Convert stylist-client relationships into firm-level partnerships. Our stylists already dress women at companies that could become full accounts; systematizing that path is one of the fastest routes to scale
• Equip stylists with the playbook and collateral to identify, open, and hand off corporate opportunities in their own markets
• Design repeatable partnership programs across corporate gifting, team uniforms, incentive and recognition rewards, and women's leadership initiatives
• Build corporate account management: reorders, new-hire onboarding, seasonal refreshes, and renewals

Key Account Management

• Own the most strategic client and corporate relationships end to end
• Ensure every account receives the personalized service this brand is built on

Performance & Insight

• Define and track the KPIs that matter, starting with stylist productivity and retention
• Use the data to reallocate coaching, coverage, and effort toward what's producing

Collaboration

• Partner closely with the Founder on brand, product, and go-to-market
• Bring field insight back into merchandising and production planning

What Success Looks Like

First 90 days. Full command of the business and a personal relationship with every stylist. Clear read on who's performing, who needs support, and where coverage gaps exist. Operating rhythm in place.

First 6 months. Stylist productivity trending up and a repeatable onboarding and training model running. New stylists added in priority markets. Corporate pipeline built and first pitches underway.

First 12 months. A measurably stronger, larger, and more productive network with strong retention. Corporate revenue meaningfully up year over year. A clear plan for year two.

Qualifications

Required

• 7–10+ years in sales, with 5+ years leading and developing sales teams
• Proven success building, coaching, and retaining a distributed, remote, or independent sales force, this is the core of the role
• Demonstrated ability to raise individual seller productivity, not just manage to a number
• Track record in apparel, luxury, or another considered-purchase category with a high-touch, relationship-driven sales motion
• Experience growing a B2B or corporate sales channel
• Exceptional communication skills; credible coaching a stylist and pitching a Chief People Officer alike
• Analytical, comfortable owning a forecast and making decisions from the numbers
• Willingness to travel regularly for market visits, coaching, client meetings, and industry events

Preferred

• Experience with commission-based or independent stylist, consultant, or advisor networks
• Experience selling into corporate gifting, uniform, or employee recognition programs
• Bachelor's degree in Business, Marketing, or a related field; MBA a plus
• Fluency with CRM and sales enablement tools

Who thrives here. A developer of people first and a closer second. You get more satisfaction from a stylist's breakthrough month than from your own. You're as comfortable coaching and helping someone grow their Midnight Oil business. And you believe what a woman wears into the room changes how the room responds, because that belief is what you'll be teaching.

Compensation & Benefits

• Competitive base salary with meaningful performance bonus tied to network productivity and revenue growth
• Flexible, remote-first working environment
• Real professional growth as the company scales
• Exclusive employee discount on Midnight Oil Collection

How to Apply

Send your resume and a short note covering two things: a sales team you built or turned around and what changed under you, and why this brand and this mission resonate with you.

Apply through our LinkedIn posting or email View email address on click.appcast.io

Equal Opportunity Employer

Midnight Oil Collection celebrates diversity and is committed to an inclusive environment for all employees. We are an equal opportunity employer.