Sales Development Representative

Paystone•, MA

4d•Remote

About The Position

At Paystone, growth starts with people, both the businesses we serve and the team members who power our mission. We are building the future of Customer-Driven Growth, helping merchants across North America deliver exceptional customer experiences and turn everyday transactions into lasting relationships. Guided by our core values, Put People First, Solve Impactful Problems, and Build a Better Future, we are redefining what it means to grow a business in today's market. We are looking for a Sales Development Representative (SDR) who thrives in a dynamic, results-driven environment. This is a key role within our growth engine, connecting with business owners, opening conversations, and setting the stage for meaningful partnerships that drive success. As an SDR at Paystone, you will take the lead in outbound prospecting and opportunity generation. You will connect with potential clients through strategic cold calling, email outreach, and social engagement, sparking interest in Paystone's suite of integrated payment and customer engagement solutions. You will collaborate closely with Account Executives to build a healthy sales pipeline, qualify leads, and ensure each handoff sets both the client and our team up for success. This role requires curiosity, resilience, and exceptional communication skills. It is the ideal fit for someone who loves building relationships and thrives on turning curiosity into opportunity.

Requirements

Previous experience in a sales or business development role with demonstrated success in lead generation or client engagement.
Exceptional verbal and written communication skills with the ability to explain value clearly and persuasively.
Strong time management skills with the ability to handle multiple priorities and hit targets, including a goal of 4 qualified meetings per week.
A proactive mindset with a commitment to continuous improvement and personal accountability.
Comfortable using CRM systems (e.g., HubSpot, Salesforce) and outreach tools to manage and track activity.
Skilled in researching target markets, identifying opportunities, and crafting outreach strategies.
Fluent in English required.

Nice To Haves

Higher education in Sales, Marketing, or Business is an advantage.

Responsibilities

Identify and connect with potential customers that fit our Ideal Customer Profile (ICP).
Conduct high-volume outreach via phone, email, and social channels, maintaining 80+ dials per day to generate qualified leads.
Research organizations and decision-makers to personalize outreach and strengthen engagement.
Qualify inbound and outbound leads to ensure strong alignment before handoff to Account Executives.
Execute live call transfers to Account Executives when prospects are ready to engage.
Manage lead progression through the sales funnel using CRM tools, ensuring data integrity and visibility.
Collaborate with Account Executives to develop territory strategies and drive pipeline growth.
Share insights, ideas, and best practices with your peers to strengthen team performance.
Maintain consistent follow-up with all leads to nurture relationships and keep opportunities moving.