SDR

We are hiring a Senior Sales Development Representative to help build Enumerate’s outbound sales engine from the ground up. This is not a role where you sit back and wait for a playbook to be handed to you. You will be prospecting, qualifying, and booking meetings for our AE team while helping shape the processes and strategies that define how we go to market. We are not looking for a polished resume. We are looking for raw talent, competitive fire, and the kind of work ethic that cannot be taught. If you have the drive to be great at this, we will give you the tools, coaching, and career path to get there. 

What You’ll Do 

Pipeline Generation 

• Own outbound prospecting into Enumerate’s ICP: property management companies that manage HOA and COA communities 

• Build and maintain a qualified pipeline of meetings for the AE team through multi-channel outreach including phone, email, LinkedIn, and video 

• Qualify inbound leads and route them to AEs with the context and discovery that makes handoffs seamless 

• Conduct conversations that surface pain points, buying signals, deal context, and community count to set AEs up for success 

Process & Strategy 

• Help build and refine outbound cadences, messaging, and targeting strategies alongside the VP of Sales and Head of Demand Generation 

• Test new approaches constantly: new channels, new messaging angles, new tools. What works stays, what doesn’t gets replaced 

• Provide frontline feedback on what prospects are saying, what objections come up, and where the pitch lands or falls flat 

• Document what works so the playbook gets sharper every week 

Technology & AI 

• Use modern sales tools (CRM, sequencing, prospecting platforms) to work smarter and faster 

• Lean into AI-powered tools for research, personalization, and outreach as part of your daily workflow 

• Bring ideas to the table on how to use technology to multiply your output and improve your results 

Who You Are 

What Matters Most 

• Tenacity around being the best. You have an internal standard that will not let you settle. Second place is not interesting to you. 
• High competitive drive and energy. You bring intensity every day, not in bursts, but as a baseline. Your work ethic is visible and contagious. 
• Willingness to test and try new strategies. You do not wait for someone to tell you what to do next. You try things, learn fast, and adjust. 
• Figure-it-out mentality. When something is unclear, undefined, or messy, you do not freeze. You move. Ambiguity is where you do your best work. 
• Self-starter who does not need a lot of direction. Give you a target, a territory, and a set of tools and you will find a way to produce results. 

Experience & Background 

We care far more about who you are than where you have been. That said, here is what will help you hit the ground running: 

• Some professional experience in a customer-facing, sales, or business development role (formal SDR experience is not required) 

• Comfort picking up the phone and having real conversations with strangers 

• Strong written and verbal communication skills. Your outreach should read like a human wrote it, not a template 

• Familiarity with CRM tools (Salesforce preferred) or a willingness to learn them quickly 

• Curiosity about AI and sales technology and a desire to use them as daily tools, not buzzwords 
• A track record of competing and winning at something, whether that is in sales, sports, school, or life