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Chicago + Remote: We have a solid footprint in Chicago, but we also hire exceptionally talented people who reside elsewhere.

We love the friendships we've forged in our Chicago office. But let's be real; things have changed. We don't plan to all return 100% in-office, but our office and gym are open on an optional basis for all employees who feel comfortable, including happy hours and team events. However, because culture and relationships are important to us, all candidates should be open to being in-office with their teams at pre-arranged times throughout the year. The specifics vary by role, so please discuss your plans with the hiring team.

Hi, welcome to PerkSpot. We’re looking for a take-charge, confident Director of Sales to join our team and run our Sales Department to new heights.

At PerkSpot, we’re proud to extend benefits and perks to a robust client base. As our Director of Sales, you will be in charge of all things commercial sales and making sure their needs are met when it comes to people, processes, and required tools. You’ll also supervise the team and report on important KPIs that determine the success of the department and PerkSpot as a whole. Your managerial skills coupled with a commitment to your team’s success will directly impact the accomplishments of the company.

About PerkSpot

PerkSpot is an employee benefits company that works with America’s top employers to offer exclusive discounts, rewards, and recognition to millions of employees. These exclusive perks and savings are a great recruitment and retention tool that allows employees to take advantage of unique opportunities and feel great about the company they work for. We help employees from over 1,000 companies like Spotify, Walgreens, McDonald's, and Lyft save on everything from gym memberships and movie tickets to electronics, new cars, and travel.

Profitable and growing, our company was founded in 2006 by good people with a great vision, and we’re carrying on the work they started. In 2018, our company was proud to announce an additional investment of $50 million dollars from Susquehanna Growth Equity. As we continue to grow, we’re excited about our leadership position in the industry, but we’re also committed to doing more - developing better products, reaching more employers, and getting more employees engaged with our platform. Our passion is to make every place a great place to work, starting with our own. We’re a big platform, but a small team. That means we’re going to trust you with more responsibility than you’d have anywhere else and invest in your success and growth more than any other employer.

Meet the Sales Team

Our Sales team is comprised of outgoing, proactive individuals who are proud to function as PerkSpot’s main brand ambassadors. Through management of AEs and Sales Managers, you will provide sales coaching, monitor team growth, and share KPI reports with company leadership telling the story of our Sales success. This is a great opportunity for someone with in-depth experience in sales and team management to handle one of the largest and most impactful departments here at PerkSpot.

Life as the Director of Sales:

• Functioning as the main representative of the Sales team to leadership and executives
• Providing regular sales trainings on best practices, deal strategy, and the sales process
• Setting business goals and ensuring the sellers and managers are aligned with them
• Coaching team managers on leadership and management strategies
• Monitoring team and individual KPIs including but not limited to: growth in eligible members and addressable members, improvement in win rate, and decrease in sales cycle time
• Monitoring important team stats such as employee turnover, department growth, improvement in win rate, and % of team reaching targeted quota
• Determining proper reporting and performance evaluation criteria in partnership with Sales Ops and Business Intelligence
• Conducting regular sales meeting and call audits to identify and remedy gaps in knowledge, sales technique, and/or inconsistencies
• Overseeing Quarterly Business Reviews
• Keeping a pulse on sales trends in the marketplace and bringing these trends to PerkSpot’s sales process
• Running regular team and staff meetings to go over company goals, success benchmarks, and sales strategies

What we’re looking for:

• At least 5-7 years of experience managing a sales team, with at least 3 of those years overseeing sales managers
• Experience advocating on behalf of a sales team; C-level communication skills a must
• Demeanor and attitude necessary for running a large sales team
• Background in HR services providers and/or enterprise sales
• Bachelor’s degree required; Masters strongly preferred
• Excellent communication, organization, and time management skills
• No issues delegating or working autonomously - micromanagers need not apply!
• Strong sales aptitude and experience managing KPIs
• Highly adaptable and collaborative work ethic
• Understanding of the PerkSpot brand and how it can positively affect lives
• Thoughtful and strategic approach to deal making and decision making
• Proactive and diligent work ethic
• Proven understanding of PerkSpot’s values as a whole and a willingness to work hard to achieve overall company goals

Your First Few Months

Culture fit is big at PerkSpot, which is why you’ll spend the first few weeks of your tenure learning the product, your job expectations, and our sales process. From there, you will begin to interact with the company’s executives and develop a strategy for KPI reporting and team management. After that you will meet with each manager separately, to effectively gauge where they need support and find them that support ASAP. Soon you’ll be running the sales team to new heights, and be the in-house expert on all things sales.

The Perks of Working at PerkSpot

We’re a big platform, but still a small team. That means we’re going to trust you with more responsibility than elsewhere, and invest in you more. You’re going to grow – a lot.

We work out of our office in Chicago’s River North neighborhood. When we are in the office, we dress how we like, encourage flexible hours and an open time-off policy, stock a good beer selection, and we’re pretty obsessive about our coffee. Most of all, we welcome good people with lots of energy and enthusiasm.

PerkSpot offers the full suite of benefits you’d expect from a profitable, established company, including health and dental insurance, a generous parental leave policy, 401(k), pre-tax transit benefits, and fully-funded disability coverage. We have in-office bike storage, a private gym, and a shower on-site.

We hold weekly company get-togethers where we learn from what went wrong and celebrate what went right. Every week at PerkSpot, we aim a little higher and get a little bit better than the previous week.

Because we consider every member of our team to be a fundamental part of our success, we encourage everyone to be invested in our success, regardless of their position. We want every one of our employees to think like an owner: put in the effort to exceed expectations, solve problems before they come up, and always go the extra mile. It’s this drive to succeed that makes PerkSpot such an interactive and fulfilling place to work.

How to Apply

All applications will be kept strictly confidential. Please submit a resume AND cover letter (we know it is old school, but a cover letter is very important to us) telling us how you stack up to the qualifications, plus any other information you feel would be relevant to PerkSpot. Don’t be afraid to show your spark and personality!

All positions require a full background screening.

Offering a diverse, equitable, and inclusive culture is a priority at PerkSpot. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, or national origin, disability or protected veteran status, or any other legally protected basis, in accordance with applicable law.