Enterprise Sales Executive - Perk (Boston, MA)

Role Overview

As an Enterprise Sales Executive at Perk, you will be at the forefront of revolutionizing how businesses manage their travel and expenses. This role is based in Boston, Massachusetts (with potential for Chicago), and focuses on driving new business acquisition within the North American market. You will manage both inbound and outbound leads, conduct compelling product demonstrations, and guide prospects through the entire sales cycle, from initial contact to closing the deal. Your success will hinge on your ability to understand customer needs, effectively communicate the value of Perk's solutions, and build lasting relationships. This role blends lead generation, account management, and strategic sales to fuel Perk’s ambitious growth objectives.

A Day in the Life

Your typical day will involve a mix of strategic outreach and responsive engagement. You’ll start by reviewing new inbound leads and planning outbound prospecting activities. A significant portion of your day will be spent on the phone, connecting with potential clients, understanding their challenges, and presenting tailored solutions. You’ll conduct product demonstrations via web conferencing, showcasing Perk’s innovative features and benefits. You will also be responsible for meticulously updating Salesforce with interaction details and prospect information. Furthermore, collaboration with the marketing team to refine lead generation strategies and improve qualification processes will be key to optimizing your sales pipeline. Closing deals and onboarding new clients will be your ultimate focus, ensuring a seamless transition and setting the stage for long-term partnerships.

Why Boston/Chicago?

Boston and Chicago represent strategic hubs for Perk due to their vibrant business ecosystems and access to top talent. Boston boasts a thriving tech scene, a highly educated workforce, and a concentration of enterprise clients that align with Perk’s target market. Similarly, Chicago offers a diverse economy, a robust transportation infrastructure, and a growing number of companies seeking innovative solutions for travel and spend management. Having a presence in these key locations allows Perk to tap into local networks, build stronger relationships with clients, and attract ambitious sales professionals eager to make a significant impact. Moreover, these cities provide a high quality of life, making them attractive destinations for career-minded individuals.

Career Path

The Enterprise Sales Executive role at Perk is a launching pad for significant career advancement within the organization. Successful executives can progress into Senior Sales roles, taking on larger territories and managing more complex accounts. Opportunities also exist to move into Sales Management, leading and mentoring teams of sales professionals. High-performing individuals may also explore paths into strategic roles such as Sales Operations or Customer Success, leveraging their deep understanding of the sales process and customer needs to drive broader organizational impact. Perk values internal promotion and provides ample opportunities for employees to grow their skills and expand their responsibilities.

Salary & Benefits

The compensation for the Enterprise Sales Executive role is competitive, with a base salary range of $120,000 to $200,000, complemented by a performance-based commission structure that rewards exceeding sales targets. In addition to competitive pay, Perk offers a comprehensive benefits package designed to support employee well-being and professional development. This includes comprehensive health insurance (medical, dental, and vision), paid time off (including vacation, sick leave, and holidays), a retirement plan with company match, employee stock options, wellness programs, and a professional development budget. Perk is committed to providing a supportive and inclusive work environment where employees can thrive both personally and professionally.

Perk Culture

Perk is more than just a company; it’s a community of passionate individuals driven by a shared mission to transform how businesses work. Our culture is built on a foundation of ownership, collaboration, and a commitment to delivering a 7-star experience to our customers. We value curiosity, purpose, and a growth mindset, empowering employees to unlock their full potential. At Perk, you’ll be surrounded by talented colleagues from diverse backgrounds, representing over 70 countries. We foster an environment where innovation is encouraged, feedback is valued, and every team member has the opportunity to make a real impact. Regular team-building activities, social events, and opportunities for professional development further enhance our vibrant and engaging culture.

How to Apply

If you are an ambitious, driven, and energetic sales professional with a proven track record of success, we encourage you to apply for the Enterprise Sales Executive role at Perk. To apply, please submit your resume and a compelling cover letter through our online application portal. In your cover letter, highlight your relevant experience, your passion for sales, and your alignment with Perk’s values. Be sure to showcase your accomplishments in lead generation, client acquisition, and relationship building. We are looking for individuals who are eager to contribute to our mission and thrive in a fast-paced, dynamic environment. The application process includes an initial screening, followed by interviews with the hiring manager and other key stakeholders. Selected candidates will then participate in a final interview and a background check. We look forward to receiving your application and learning more about your qualifications.

FAQ

1. What is Perk?

   Perk is the intelligent platform for travel and spend management, automating everything from travel bookings to expenses and invoice processing.

2. What are the main responsibilities of an Enterprise Sales Executive?

   Managing leads, presenting demos, closing deals, understanding prospect needs, and maintaining Salesforce records.

3. What skills are important for this role?

   Sales, lead generation, negotiation, communication, and relationship-building skills are crucial.

4. What is the company culture like at Perk?

   Perk has a fun, challenging, and collaborative culture that values ownership and a 7-star experience.

5. What kind of career growth can I expect at Perk?

   Opportunities for advancement into senior sales roles, management positions, and strategic operations roles.

6. What benefits does Perk offer?

   Comprehensive health insurance, paid time off, retirement plan, stock options, and professional development opportunities.

7. Where is this role located?

   This role is based in Boston, Massachusetts, with possible consideration for Chicago, Illinois.

8. What kind of experience is needed for this role?

   Proven track record in B2B sales, lead generation, and client acquisition through prospecting and outbound activities.

9. How does Perk support employee development?

   Perk provides a professional development budget, opportunities for training, and encourages internal promotion.

10. What makes Perk a great place to work?

    Perk offers a supportive, inclusive environment, a chance to work with a global team, and the opportunity to make a real impact.