Senior Sales Development Representative

Flippa.com; Wakefield; Hybrid; USD 60,000 - 100,000; Full time

Job summary

An established industry player is seeking a Senior Sales Development Representative to lead their outbound prospecting initiatives. This role is perfect for a motivated individual with a proven track record in sales development, adept at engaging decision-makers and generating quality leads. You will leverage tools like Salesforce to manage outreach, collaborate with teams, and mentor fellow SDRs. Join a dynamic environment where your contributions will drive success and growth, while enjoying a competitive salary and comprehensive benefits package.

Benefits

PTO (vacation, sick, personal time)

12 Paid Holidays

401(k) Plan with Company Match

Community Volunteer Days

Medical, Dental, Vision

Life Insurance

Parental Leave

Qualifications

• 2+ years of experience in Sales Development or Business Development.
• Proven ability to generate and qualify leads in a B2B environment.

Responsibilities

• Drive outbound prospecting efforts to generate high-quality leads.
• Manage and optimize outreach efforts using Salesforce.

Skills

Sales Development

Communication Skills

Outbound Prospecting

Active Listening

Customer Empathy

Education

Bachelor’s Degree

Equivalent Work Experience

Tools

Salesforce

LinkedIn

ZoomInfo

Marketing Automation Tools

Job description

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 successful track record 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. You will build and grow relationships across channels such as employee benefit brokers, retirement plan advisors, CPAs, ERISA attorneys, CEOs, CFOs, and HR leaders. Your focus will be 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 effectively to address customer challenges.
• Build industry knowledge and insights on market trends, services, products, positioning, and sales concepts.

The Behaviors You Bring:

• Integrity – Demonstrate genuine customer empathy and uphold a customer-centric approach.
• Expertise – Be a team player who seeks opportunities to learn, share knowledge, and improve processes.
• Empowerment – Independently manage priorities, deadlines, and challenges with strong organizational skills.
• Excellence – Maintain a detail-oriented mindset to ensure quality results and build rapport through effective communication.
• Innovation – Adapt quickly, collaborate effectively, and propose ideas to enhance operations.

The Excellence You Deliver:

• 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 and active listening to assess prospect needs and opportunities.

Base salary is $60,000 annually plus incentive bonus with on-target earnings up to at least $99,600.

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 within our company. Being part of this company means being 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 Award from Energage.

At Sentinel, we hire people with diverse experiences, backgrounds, and perspectives. Even if you don’t meet every requirement, please consider applying if you like what you see. Our priority is to find talented individuals who can contribute to our team culture and are excited about their work.

Sentinel is an equal opportunity employer. If you need reasonable adjustments during the application or interview process, please let us know.

Some of our Benefits:

• PTO (vacation, sick, personal time)
• 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 serves nearly 5,000 clients nationwide. For over 35 years, we've been committed to positively impacting our people, clients, and communities. With an average tenure of 9 years among our 265 professionals, our team’s dedication to excellent service has made Sentinel the only provider that makes benefits EASY: easy for your people, easy for your business, and easy for you.

Our goal is to help companies and employees prepare for future health, wealth, and retirement needs through simple, continuously improved solutions. Our in-house experts exemplify who we are.

Sentinel is among Massachusetts’ largest employee benefits firms (Boston Business Journal) and was named a 2022 Retirement Plan Adviser of the Year in the Mentorship category (PLANADVISER Magazine).