Senior Sales Development Representative

Location Note : This is a hybrid role for our Wakefield, MA office. The Purpose of Your Role : We are seeking a Senior Sales Development Representative (SDR) to drive our outbound prospecting efforts and generate high-quality leads for our Sales team. This role is ideal for a highly motivated individual with a track record of success in sales development, strong communication skills, and the ability to engage decision-makers effectively. Leveraging Salesforce and other tools, you will manage and optimize outreach efforts to engage with multiple buyer personas and roles, introducing Sentinel’s value. In this role, you will build and grow relationships across channels such as employee benefit brokers, retirement plan advisors, CPAs, ERISA attorneys, CEOs, CFOs and HR leaders. You will focus on generating qualified meetings and pipeline opportunities for the Sentinel Sales team while mentoring fellow SDR team members. This role offers personalized sales coaching to help you develop and refine your sales approach. The Expertise We’re Looking For : Effectively manage outbound prospecting initiatives through Salesforce. Conduct high-level discovery conversations within target accounts. Meet or exceed SDR-sourced Qualification Call (QC) volume targets. Collaborate with teammates to develop targeted lists, call strategies, and messaging. Utilize Salesforce to research accounts, identify key players, generate interest, and track activity. Proactively engage with leads through diverse outreach methods, including at least 100 cold calls per day, targeted emails, social media interactions, in-person meetings, and industry events to drive pipeline growth. Manage, track, and report activities and results within Salesforce. Assist in documenting and updating the Sentinel SDR Playbook. Partner with Sales & Marketing to drive attendance at prospect events. Represent Sentinel at networking events to identify opportunities and schedule meetings. Act as a mentor for new SDR hires, helping them navigate key accounts. Communicate Sentinel’s value proposition and how it addresses customer challenges effectively. Demonstrate understanding of the benefits industry and competitive landscape by building expertise of services, products, positioning, and sales concepts while gaining industry knowledge and insights on market trends The Behaviors You Bring : Integrity – You demonstrate genuine customer empathy and uphold a customer-centric approach. Expertise – You are a team player who seeks opportunities to learn, share knowledge, and improve processes. Empowerment – You independently manage priorities, deadlines, and challenges with strong organizational skills. Excellence – Your detail-oriented mindset ensures quality results, and your communication skills build rapport. Innovation – You adapt quickly, collaborate effectively, and propose ideas to enhance operations. The Excellence You Deliver : You collaborate effectively with Sales and marketing teams to align outreach strategies. Implement best practices in Salesforce to maintain data integrity and expand market reach. Demonstrate positive and energetic phone skills, active listening, and strong writing abilities. Show self-motivation and a history of credible achievements. Display knowledge of business processes, roles, and organizational structures. Exhibit resilience and a results-driven personality. Proficiency in Salesforce, LinkedIn, and other sales enablement tools. Experience in sales development, sales, or the financial services industry is a plus. About You : We are looking for an innovative thinker with an entrepreneurial spirit, customer focus, and the determination to challenge the status quo. The financial services industry evolves rapidly, and we seek someone adaptable and open to change. Education, Skills, and Experience : Discipline to stay focused on the defined lead qualification process. Tenacity to persevere through challenges and secure results. Active listening skills to identify prospect needs and opportunities. Ability to conduct detailed prospect and account research using Salesforce, LinkedIn and ZoomInfo. Familiarity with marketing automation tools to personalize outbound communication. Knowledge of social media platforms for account monitoring and identifying trigger events. Proven ability to manage multiple tasks and meet deadlines. Preferred Qualifications : 2 years of experience in a Sales Development or Business Development role. Proven ability to generate and qualify leads in a B2B environment. Strong written and verbal communication skills. Experience using Salesforce and sales engagement tools. Self-motivated, goal-oriented, and eager to contribute to team success. Ability to thrive in a fast-paced, dynamic sales environment. Bachelor’s degree from an accredited college or university or equivalent work experience Excellent interpersonal skills Active listening to assess prospect needs and opportunities What You’ll Be Part Of : Our people care about our organization. We are a company with a mission to be the best in our industry and best within our company. Being part of this company means that you are part of something special.    Sentinel was recently recognized by The Boston Globe as a Top Place to Work in 2020. In 2021, 2022 & 2023, Sentinel earned a Top Workplace USA Awards from Energage. At Sentinel, we hire people with all kinds of awesome experiences, backgrounds, and perspectives. We like it that way. So even if you don’t meet every single requirement, please consider applying if you like what you see. Our priority is to find the brightest talent that can add to our team culture, those who actively contribute and who are excited about what they do. Sentinel is an equal opportunity employer and welcomes everyone to our team. If you need reasonable adjustments at any point in the application or interview process, please let us know. Some of our Benefits : PTO (vacation, sick, personal time bank) 12 Paid Holidays (10 stated and 2 floating holidays) 401(k) Plan with 3.75% Company Match 2 Community Volunteer Days 5 Summer Half Days Medical, Dental, Vision Life Insurance LTD & STD Parental Leave See What We Stand For : https : / / www.sentinelgroup.com / About-Us / Join-Our-Team Who we are : Sentinel Group proudly serves nearly 5,000 clients throughout the U.S. For 35 years, we’ve remained devoted to positively impacting the lives of our people, our clients and our communities. With a 9-year average associate tenure among our 265 professionals, our team’s commitment to excellent service has positioned Sentinel as the only provider who makes benefits EASY : easy for your people; easy for your business; and easy for you. Our ultimate goal is to help companies and their employees prepare for their future health, wealth and retirement needs. Whether it’s through retirement plans, group health insurance, reimbursement accounts or financial planning, we engineer simple solutions and continuously strive to make them better. Our in-house experts – and their commitment to excellence – define who we are. Sentinel is also one of the largest employee benefits firms in Massachusetts (Boston Business Journal) and was named a 2022 Retirement Plan Adviser of the Year in the Mentorship category (PLANADVISER Magazine).   Powered by JazzHR