Sales Development Representative - In Market; Bay Area

Overview

At Side, we believe everyone should own their path. Side partners with top-producing real estate professionals to help them own and operate their own boutique real estate companies, without the legal, regulatory, or operational complexity of running a traditional brokerage. As a pioneer in the Brokerage-as-a-Service model, Side provides a proprietary platform that increases efficiency, strengthens client relationships, and enables entrepreneurs to focus on what they do best — selling real estate and growing their businesses.

Headquartered in San Francisco and backed by more than $300 million from top-tier venture capital firms, Side is recognized as one of the most innovative and fastest-growing companies in real estate. At Side, you’ll work alongside experienced industry leaders and world-class engineers to help shape the future of real estate and empower exceptional professionals to thrive as business owners.

About the Role

This isn’t a generic SDR seat. You’ll be dialing directly to decision makers — top-producing real estate agents doing $20M–$100M+ in annual volume who think like business owners, not salespeople. No gatekeepers, no middle managers. Your job is to earn their attention and book high-quality intro calls for our Ambassadors (Account Executives). You’ll sit on a lean, high-impact sales team (2 SDRs, 2 Ambassadors) reporting directly to the Head of Sales, with real visibility into deal strategy and direct exposure to enterprise-level conversations.

• Dial directly to decision makers — you’re not calling gatekeepers or office managers. You’re picking up the phone and reaching top-producing agents and team leaders ($25M+ annual volume) who own their business.
• Execute 75+ daily touches by phone to maintain a steady flow of qualified conversations with real decision makers.
• Research prospects before outreach — know their production, team size, current brokerage, and what’s likely keeping them stuck. Personalize every touchpoint so it lands.
• Book 15–20 qualified intro calls per month for our Ambassador team with agents who fit Side’s ideal partner profile.
• Qualify prospects against clear criteria: production volume, team size, brand ambition, and readiness to move. No vanity meetings.
• Own the handoff — prep Ambassadors with context on every booked call so they walk in informed.
• Drive attendance to Side-hosted events, activations, and experiences by personally reaching out to target agents and industry leaders.
• Represent Side at industry events and conferences — build your network and identify high-potential prospects in person.
• Maintain meticulous records in Salesforce — every touch, every conversation, every outcome logged in real time.
• Collaborate with Marketing and Sales leadership to align outreach with campaigns, events, and strategic priorities.

• 2+ years in sales development, business development, recruiting, or a high-volume customer-facing role. You’ve hit quota before and know what daily discipline looks like.
• Exceptional communication skills — written and verbal. You can write a 3-sentence cold email that gets a response from a $50M producer and hold your own on a call with a seasoned entrepreneur.
• High activity tolerance. 75+ calls/day doesn’t scare you — it’s how you build a pipeline.
• Self-starter mentality. You don’t wait to be told what to do. You find the gap, fill it, and tell your manager after.
• Strong organizational skills and CRM hygiene.
• Salesforce is your second home.
• Genuine curiosity about real estate as a business. You don’t need to have sold homes, but you should be interested in how top agents build and scale their businesses.

• Real estate industry experience — brokerage, proptech, mortgage, title, or adjacent.
• Experience selling to entrepreneurs, business owners, or high-net-worth individuals (not just mid-market or enterprise IT buyers).
• Familiarity with Salesforce, and outbound sequencing tools.
• Track record of exceeding SDR metrics (meetings booked, pipeline generated, conversion rates).

• You’re calling the decision maker directly. No gatekeepers, no procurement teams, no layers…