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Senior Business Development Representative

RiffleCM, Chicago, Illinois, United States

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RiffleCM is creating a comprehensive platform tailored specifically for subcontractors to streamline their bidding and project execution processes. By automating workflows, enhancing visibility, and delivering precise pricing, RiffleCM helps subcontractors and trade partners eliminate errors and save valuable time. Designed "by the trades for the trades," the platform empowers users to bid smarter, win more projects, and generate revenue effectively.

The Role We are looking for an experienced BDR to drive outbound engagement and help prospects take the critical first step to utilizing RiffleCM and experiencing value.

This is a high-activity, high-ownership role focused on trust-building, qualification, and activation. You are not negotiating contracts or running long demos. Your job is to get the right people into the product and set them up for success.

What You Will Do

Run high-volume outbound outreach via email and phone to a defined ICP

Qualify prospects quickly and clearly

Handle objections related to inbox permissions, security, and trust

Drive prospects to connect their Gmail or Outlook inbox

Book short calls when helpful, but prioritize fast activation

Maintain clean CRM notes and funnel hygiene

Share real-time feedback on messaging, objections, and patterns

Collaborate closely with the CEO and product team

What Success Looks Like

Inbox connections, not meetings, are your primary win metric

Consistent outbound activity with strong response rates

Clear documentation of objections and how they are handled

High-quality activated accounts handed off to product-led conversion and founder sales

Tight feedback loops that improve scripts and sequences over time

Who You Are

2–5 years of BDR or SDR experience in B2B SaaS

Comfortable with phone-heavy and email-heavy outreach

Strong communicator who can explain technical concepts simply

Calm and confident addressing security and access concerns

Organized, coachable, and process-driven

Not ego-driven and not dependent on complex deal cycles

Comfortable selling an early-stage product that is improving fast

Nice to Have

Experience selling to SMBs or trades-based businesses

Experience supporting PLG or free-trial motions

Familiarity with Gmail or Outlook permission models

Experience working directly with founders

Compensation

Performance-based incentives tied to activation metrics

Opportunity to grow into early AE, sales ops, or player-coach roles as the team scales

Why Join Now

Early impact on how sales is built from the ground up

Direct access to leadership and product decisions

Clear ownership over a critical growth lever

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