Sales Development Representative (SDR)

Overview

You're booking demos for Account Executives by prospecting into healthcare practices—mostly medical offices and dental practices. You spend your day cold calling office managers, practice administrators, and sometimes doctors directly to schedule meetings. Rectangle Health sells payment processing and patient billing solutions to healthcare providers.

Role Snapshot

Company Context

Stage: Mature/established (324 employees, no recent funding news indicates private equity backed or bootstrapped)

Size: 324 employees

Growth: Actively hiring SDRs across multiple Florida offices, VP directly recruiting indicates expansion

Market Position: Established player in healthcare payments/fintech space competing in a crowded vertical

GTM Reality

Pipeline Sources:

• 80% Outbound - cold calling into assigned territories of healthcare practices, email sequences, LinkedIn outreach to practice administrators
• 15% Inbound - some website leads and referrals from existing customers
• 5% Events/Conferences - healthcare industry trade shows

SDR/AE Structure: Dedicated SDR team feeding qualified meetings to AEs

SE Support: Unknown, likely no SE involvement at SDR stage

Competitive Landscape

Main Competitors: Other healthcare payment processors, general merchant services providers, practice management software with integrated payments

How They Differentiate: Healthcare-specific payment solutions vs generic processors, likely emphasize compliance and patient experience

Common Objections: "Happy with current processor," "Too busy to switch," "What's the cost to change systems," "Need to talk to my partner/spouse"

Win Themes: Healthcare specialization, patient payment experience, compliance built-in, potentially better rates

What You'll Actually Do

Time Breakdown

Cold Calling (50%) | Email/LinkedIn (25%) | CRM/Admin (15%) | Team Meetings (10%)

Key Activities

• Dialing: 60-80 calls per day to healthcare practices. You're trying to get past the front desk to reach the office manager or practice administrator. Most calls go to voicemail or you get "they're with a patient."
• Email Sequences: Building and sending templated sequences to prospects. Personalizing subject lines and opening sentences for your territory. Response rates are low (2-5%).
• Qualification Calls: When someone responds, you're doing 5-10 minute qualification calls to confirm they're the decision-maker, understand their current payment setup, and gauge interest level before booking the AE demo.
• CRM Hygiene: Logging every call, email, and outcome in Salesforce (or similar). Updating lead status, taking notes on conversations, tracking touch attempts. This takes longer than you'd expect.
• Pipeline Reviews: Weekly or bi-weekly syncs with your manager reviewing numbers, listening to call recordings, and getting coaching on objection handling.

The Honest Reality

What's Hard

• Gatekeepers: Front desk staff are trained to screen calls. You'll get very good at leaving voicemails that never get returned. It takes 8-12 touches to reach most prospects.
• Timing: Healthcare practices are busiest when patients are there (mornings and afternoons). The best time to call is often lunch or early evening, but that's when decision-makers are also taking breaks.
• Rejection Volume: Most days you're hearing "no" or getting ignored. You need to be okay with 50+ rejections per day to get your 2-3 qualified meetings booked.
• Disqualifications: You'll book meetings that AEs later disqualify because the practice is too small, already under contract, or not the real decision-maker. This impacts your credibility.
• Repetitive: You're saying essentially the same pitch 60 times a day. The monotony is real.

What Success Looks Like

• Meeting Quota: Booking 15-20 qualified meetings per month that AEs accept and show up to
• Show Rate: 70%+ of your booked meetings actually happen (prospect doesn't cancel or no-show)
• Conversion Quality: AEs convert 25-30% of your meetings to opportunities, meaning you're qualifying properly
• Activity Metrics: Hitting 60-80 dials/day, 40-50 emails/day consistently

Who You're Selling To

Primary Buyers:

• Office Managers at medical practices (5-20 providers)
• Practice Administrators at larger groups (20+ providers)
• Dental practice owners or office managers
• Occasionally physicians or dentists who own the practice

What They Care About:

• Not disrupting patient care: They're risk-averse about changing systems mid-operation
• Staff training time: How long until their front desk is comfortable with new system
• Cost comparison: What they're paying now vs what you're offering, including hidden fees
• Patient experience: Does it make checkout easier or harder for patients
• Compliance: HIPAA and healthcare payment regulations—they need assurance you understand their world

Requirements

• Comfortable making 60+ cold calls per day to people who didn't ask to hear from you
• Thick skin—most of your outreach gets ignored or rejected
• Coachable—willing to practice scripts, take feedback on call recordings, iterate on messaging
• Based in St. Petersburg or Tampa, FL (in-office role)
• Hungry to move up—this is explicitly positioned as a path to AE and sales leadership
• No healthcare experience required, but you'll need to learn the industry quickly (practice workflows, payment pain points, compliance basics)
• 1-2 years sales experience preferred but will consider career changers who demonstrate resilience and work ethic