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FreeWill

Sales Development Representative (Estately)

Job Summary

The Sales Development Representative (SDR) role at FreeWill focuses on generating and qualifying leads by prospecting, cold calling, and email outreach to financial advisors. The SDR will support the sales team by initiating contact, scheduling discovery meetings, and helping build the sales playbook within an early-stage startup environment. Key skills required include strong communication, experience with high-volume calling, and proficiency with sales tools like Hubspot or Salesforce. This role offers a fully remote position with comprehensive benefits and a focus on collaborative, goal-driven work.

Required Skills

Communication Skills
Cold Calling
Lead Generation
Time Management
Relationship Building
Adaptability
CRM Management
Collaboration
Sales Tools

Benefits

Health Insurance
Paid Time Off
Remote Work
Parental Leave
Flexible Hours
Dental Insurance
Vision Insurance
Life Insurance
Disability Insurance
Retirement Plan (401k)
Professional Development
Company Stock Options
Referral Bonuses

Job Description

FreeWill is an award-winning, social-good startup that has partnered with 2,200+ nonprofits who support our mission while generating $11.9B in gift commitments for nonprofits since we were founded in 2017. We’ve been featured in the New York Times, Forbes, Oprah’s magazine, and our co-CEOs have even been named to Town & Country’s “Top 50 Philanthropists” list.

All of this is because we’ve figured out how to make some powerful (but complicated!) ways to donate much easier and more accessible. Our products make things easier for the donors who want to change the world and for nonprofits doing heroic work around the planet.

In the last 8 years, we’ve grown from 5 people to 200+ (all smart, tenacious, and kind), and continue to grow. We’d love to have you be a part of this adventure. In 2024, we were named a "Most Loved Workplace" by both Newsweek and Best Practice Institute and in 2025, we were named as one of Forbes' Best Startup Employers and the 2025 Most Loved Workplaces® for Diversity; you can also check us out on Glassdoor! Curious about company culture and management at FreeWill? Check out the 2025 Best Manager Ever podcast featuring Anthony Sottile, FreeWill's VP of Partner Success on either Spotify or Apple.

Full-time • Excellent Benefits • Work from Anywhere in the US (except AL, CO, LA)

About the Role

FreeWill is revolutionizing estate planning with Estately, a new platform for financial advisors (FAs). We're searching for a passionate Sales Development Representative (SDR) to join our mission and build a thriving sales channel from the ground up. The Estately team functions as an early stage startup within a larger startup. This is a fast-moving, high velocity deal role selling into financial advisor firms of various sizes. The SDR will also help build the SDR playbook for Estately.

As an SDR, you will be responsible for generating and qualifying leads to support the founding Estately sales team in achieving revenue targets. Your primary focus will be on prospecting, outbound lead generation, and initiating contact with potential FreeWill partners. You will play a crucial role in the sales process by identifying qualified opportunities and passing them on to the appropriate account executives. The SDR role requires excellent communication skills, a strong work ethic, and the ability to thrive in a fast-paced, target-driven environment.

This role will need to work during general business hours which is typically 9-5pm EST or 7-3pm PST.

FreeWill has set compensation and a non-negotiation policy for fairness reasons (we don't think that an individual's pay should be determined by how comfortable they are negotiating). As a result, we like to be transparent and up front about the compensation. The offer for this role will be a yearly base salary of $70,000. This role is not eligible for commission.

If you are interested in the role, please apply to our website. Please do not contact recruiters/employees by email or phone.

Responsibilities

  • Build your own prospect lists of financial advisors based on our ideal customer profiles
  • Initiate contacts with prospects through cold calls (50+ per day) and email campaigns to educate them about FreeWill, generate interest, and identify new sales opportunities
  • Qualify leads and schedule discovery meetings for the sales team with interested prospects, ensuring a smooth handover of information
  • Maintain accurate and up-to-date records of all interactions and prospect information in the customer relationship management (CRM) system
  • Clearly articulate products and solutions with prospective partners to successfully manage and overcome objections
  • Create personalized outreach to target accounts to generate sales meetings
  • Collaborate closely with account executives to align on target accounts and optimize the sales process
  • Meet or exceed assigned targets for lead generation

Qualifications

  • Previous experience in sales, lead generation, or customer-facing roles is advantageous but not mandatory. Those with a passion for sales and a strong desire to learn are also encouraged to apply.
  • Ability to thrive in a fast-paced, dynamic environment and adapt quickly to changing priorities and growing team
  • Some experience with, or strong willingness to learn, sales databases and tools (such as Hubspot and Salesforce)
  • Experience with high-volume cold calling is required.
  • Ability to work independently and consistently achieve or exceed goals.
  • Excellent verbal and written communication skills with the ability to engage, persuade, and build rapport with prospects
  • Strong organizational and time management skills to handle multiple priorities with attention to detail
  • Collaborative mindset with a willingness to work closely with the sales team members & consistently engage with potential partners

Hiring Process

The hiring process for this role is as follows:

  • Candidate Introduction Video (3 minutes)
  • Hiring Manager Video Interview (15-30 minutes)
  • Mock Call (prepare on your own time; 30 minutes live)
  • Final interview with FreeWill team members (30 minutes)
  • Offer (contingent on positive references)

Please note that steps in the hiring process can and may change and the Recruiter will be your point of contact in sharing any updates in terms of the process. If you are selected to move forward in this process, the Recruiter will share more details about the hiring process and interviewers. However, this is a good estimate of what you can expect. For most roles, our hiring processes take an average of 4-6 weeks.

AI Policy

We are excited to engage with candidates who can demonstrate their experience and skills through their own words and work, not through AI-generated content. We want to understand your genuine interest in the company and your unique perspectives, not simply AI-driven responses. We ask that you refrain from use of AI-generated content during the hiring process which includes phone screens, video interviews, tech screens, or other assessment stages except as otherwise indicated to you by the Recruiter.

For example: Using ChatGPT to generate scripted answers to application questions or during phone screens and video interviews is strongly discouraged and will result in not moving forward in the hiring process. However, the use of an AI design tool to enhance the design of a presentation deck is permitted.

The Recruiter will be able to provide additional guidance during the hiring process if needed. If hired at FreeWill, we do encourage the use of AI in your role to build upon or enhance your skill set.

Benefits

In addition to the immense personal and professional satisfaction you’ll gain from helping to raise $1T for high impact nonprofits in a kind and joyful work environment, full time employees at FreeWill are eligible for the following benefits:

  • Work from home
  • Unlimited PTO
  • Flexible hours
  • Competitive salary
  • Commuter benefits
  • Company stock options
  • 401k
  • Medical/Dental/Vision (some single coverage medical plans are 100% employer paid, subsidized rates for spousal, parent-child, and family coverage)
  • Short-term and long-term disability insurance
  • Life and AD&D insurance
  • Free One Medical membership
  • Paid parental leave for all parents

Perks

  • Regular (virtual) team events
  • $250 monthly co-working budget which can be used for local co-working spaces
  • $300 annual budget to outfit your home office or cover utility bills
  • $1,000 referral bonuses for growing our FreeWill community
  • $1,000 annual professional development budget

FreeWill is an equal opportunity employer and we value diversity. We are committed to finding talent that is not determined on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by law.

We are a remote-first company. Unfortunately, we are unable to hire in Alabama, Colorado, or Louisiana at this time for this specific role. We also can’t sponsor working visas, so all applicants will need to have work authorization in the US.

Don’t check off every box in the requirements listed above? Please apply anyway! Studies have shown that marginalized communities - such as women, LGBTQ+ and people of color - are less likely to apply to jobs unless they meet every single qualification. FreeWill is dedicated to building an inclusive, diverse, equitable, and accessible workplace that fosters a sense of belonging – so if you’re excited about this role but your past experience doesn’t align perfectly with every qualification in the job description, we encourage you to still consider submitting an application. You may be just the right candidate for this role or another one of our openings!

#LI-DNP

Interested in this job?

Application deadline: Open until filled

Logo of FreeWill

FreeWill

FreeWill lets you make your last will and testament quick, easy, and completely free. It is a simple online legal will maker that helps you compile will forms to print and sign, or to take as a basic will template to an estate planning lawyer. FreeWill is built alongside will making experts.

See more jobs
Date PostedJuly 8th, 2025
Job TypeFull Time
LocationREMOTE - USA
SalaryCompetitive rates
Exciting remote opportunity (requires residency in United States) for a Sales Development Representative (Estately) at FreeWill. Offering competitive salary (full time). Explore more remote jobs on FlexHired!

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