Role Description

Investment Sales Closer at Ulysses Group, a remote, full-time position with OTE of $180,000 – $220,000+, commission-based with monthly pay. Start date: ASAP.

• Show up to pre-qualified inbound discovery calls booked by the appointment setting team — your job is to close, not to source.
• Conduct consultative discovery conversations with private equity principals, investment bankers, search fund operators, and M&A advisors.
• Present Ulysses Group's M&A lead generation offer — retainer-based, results-oriented, and tailored to each client's acquisition strategy.
• Prepare and deliver customized proposals or documents between first and second calls as part of the structured two-call sales process.
• Reach out directly to reactivation leads on a case-by-case basis — prospects previously identified as strong fits but not yet closed — to generate quick wins and build pipeline.
• Attend weekly strategy and call review sessions with the team — these are mandatory and serve as a core part of performance improvement.
• Log all call outcomes and feedback promptly using internal systems (GoHighLevel, Loom, Google Workspace).
• Report to the fractional sales manager on day-to-day sales activity, with direct access to the founder for technical and product questions.

Qualifications

• Experienced B2B closer — comfortable selling $7,000–$15,000/month retainers to C-suite executives, PE principals, and institutional decision-makers.
• Consultative and authoritative — able to establish credibility immediately with sophisticated financial buyers who will not respond to generic sales pitches.
• Proactive and detail-oriented — does not wait to be told what to do; flags issues, prepares thoroughly, and follows up without being prompted.
• Coachable and direct — receptive to feedback from the sales manager and willing to act on it; equally comfortable giving honest feedback upward.
• Organized — manages a two-call close cycle, prepares custom proposals between sessions, and stays on top of reactivation leads without losing momentum.
• Background in M&A, consulting, private equity, investment banking, or financial services is a significant plus.
• Fully committed to a full-time, commission-only structure — no base salary.

Requirements

• Closing consistently at 15%+ on qualified inbound calls — you will have a dedicated setter team booking and qualifying all calls on your behalf.
• Generating closed revenue consistently — speed to first close matters given the commission-only structure and the 3-4 week sales cycle.
• Preparing strong proposals between calls and showing up to second sessions with a clear, tailored close strategy.
• Being proactive — identifying reactivation opportunities, flagging deal blockers early, and contributing feedback that helps the team improve.
• Earning $180,000–$220,000+ annually through consistent performance at a conservative close rate and average deal size.

Benefits

• Commission-only — no base salary.
• 10% of all cash collected for the full duration of the client agreement.
• On a $7,000/month retainer: $700/month for the life of the contract.
• OTE: $180,000 – $220,000+.
• Payment: monthly.

Tools

• GoHighLevel (CRM, pipeline management, contact tracking).
• Zoom (all sales calls and team communication).
• Loom (proposal delivery and async communication).
• Google Workspace (email, Drive, Docs).
• Fathom (call recording and review).
• Claude / ChatGPT (custom report generation and call preparation).
• Slack (team communication).

Apply

Submit your resume and a short application through this platform. Selected candidates will be invited to an initial screening call with the Sales Match recruiting team, followed by a final interview directly with the Ulysses Group founder and fractional sales manager. Do not contact the company directly regarding this role.