Director of Sales, Strategic Mid-Market Sales at Wrapbook

Title: Director of Sales, Strategic Mid-Market Sales

Location: Remote – USA / CANADA

About Us:

Our mission at Wrapbook is to increase the prosperity of the project economy. A significant shift has occurred within the workforce recently and 50M Americans are now engaged in freelance or project-based work. The popularity of project based employment has introduced flexibility for both employers and employees but also added complexities from a compensation and administrative standpoint. Our vertical fintech platform enables companies to seamlessly onboard, pay and insure their workforces.

We’re building the best product for the entertainment industry but operate in a 50B market and have big goals we want to achieve. With over 130M USD raised from Andreessen Horowitz, Equal Ventures, Uncork Capital, Jeffrey Katzenberg and CAA co-founder Michael Ovitz, we are at an exciting stage of growth and there isn’t a better time to join!

The Opportunity – Director of Sales, Strategic Mid-Market Sales (Remote – Canada / USA)

We are looking for an experienced candidate to lead Wrapbook’s Strategic Mid-Market sales team and win business from commercial production companies, large brands and agencies, helping them to transform their entire production payroll process.

In this role you will lead a dynamic team of sales reps, helping them develop their skills and deliver on their ambitious targets, as well as support directly to win strategic customers.

We are looking for a proactive leader who has demonstrated success dealing with ambiguity, operating in a high-growth environment and solving problems with limited oversight. Ideal candidates will have experience managing a technology sales team focused on selling to strategic or mid-market accounts (100k+ ACV, 3-6+ month sales cycles, multiple stakeholders), and possess first-class analytical, communication and relationship-building skills.

What you’ll Do:

  • Reporting to the VP of Sales, you will be responsible for developing and leading a team of sales professionals focused on the strategic mid-market customer segment (3-6 month sales cycles, 100k+ ACV and multiple stakeholders)
  • Develop the long-term vision and strategy for the team and manage day-to-day operations, with a focus on performance against key goals.
  • Accountable for increasing revenue and new client acquisition at high rates of growth.
  • Coach and guide the team in developing consultative and solution-based sales skills through all facets of the sales cycle.
  • Play a personal and direct role in the sales process with strategic accounts.
  • Regularly report on team and individual results through pipeline management and forecasting.
  • Work collaboratively and cross-functionally with various teams to help shape Wrapbook’s products and solutions to meet customer needs (e.g., marketing, success, product, legal, etc.).
  • Participate in industry and prospect events to help support positive market awareness and increase sales.

What you’ll Have:

  • 8+ years of sales experience and 5+ years of people management experience.
  • Experience leading a sales team in a high-growth technology environment covering mid-market or strategic accounts.
  • Ability to train and coach a high-performing sales team.
  • Ability to build strategic executive relationships with customers and industry thought leaders.
  • Ability to work cross-functionally, particularly with Product and Marketing, to develop product functionality and create effective marketing plays to win clients.
  • Ability to operate in a highly ambiguous and fast-paced environment.
  • Some travel will be required (<10% of the time)

Why Join Us

At Wrapbook, creativity meets technology and not just in the product.

In addition to a competitive salary and all the benefits you can expect from a fast-growing technology company, you’ll get access to a team of creative problem solvers and the chance to see your contributions make large impacts. Benefits include:

  • Minimum Time Off: Everyone is encouraged to take at least 3 weeks off annually. An easy way to remember this policy is “take what you need, check with your lead”. It’s really that simple.
  • Work from anywhere in Canada and USA
  • Health and Dental Benefits
  • Up to $1500 towards IT set up for your home
  • Up to 4% matching RRSP / 401K
  • Learning and Development Allowance
  • $150 Monthly Lifestyle Benefits

Our Pledge to Fostering an Inclusive and Safe Workplace:

Wrapbook pledges to be a harassment- and discrimination-free space for everyone, regardless of age, disability, ethnicity, gender identity or expression, nationality, neurotype, personal appearance, political affiliation, professional background, race, religion, or sexual identity or orientation.

Apply Now

Have we got your attention? Submit your application today and a member of our Talent team will be in touch with you shortly!