Role: Sales Development Representative

Company: Hoss Tree Advisors

Commitment: Sales Development Representative (SDR)

Time Zone: Central Time (CST)

Hours: Monday to Friday, 9:00 AM – 5:00 PM

About the Role

Hoss Tree Advisors is a mergers & acquisitions advisory firm specializing in sell-side transactions for tree service and vegetation management businesses. They help owners navigate one of the most important financial events of their lives — the sale of the company they built — and run a structured, competitive process designed to maximize value and certainty of close.

We are hiring a Sales Development Representative (SDR) to drive the front end of that process: reaching business owners, opening conversations about their long-term goals, and booking qualified introductory meetings for our Managing Partners.

This is a high-volume, high-accountability outbound role and the engine of our deal pipeline. You will work from a large, pre-built database of tree service and vegetation management owners, so your energy goes into conversations — not into hunting for names. This role is ideal for someone who is comfortable on the phone all day, can hold a credible business conversation with a company owner, and is motivated by clear, measurable goals.

Key Responsibilities

• High-volume outbound calling — 75–100 outbound dials per day to business owners drawn from our existing database, using a dialer-equipped CRM (HubSpot, Outreach, or similar).
• Book 2 qualified meetings per week for the Managing Partners — the core metric of the role. Quality conversations that move a qualified owner into the pipeline.
• Pitch the firm and our M&A services — Quickly and credibly explain who Hoss Tree Advisors is, the value of a structured sell-side process, and why an owner should take an introductory call — without overstepping into advisory or valuation territory reserved for the partners.
• Basic follow-up emails — Send timely, professional follow-up emails after calls, voicemails, and connects to keep prospects engaged and confirm booked meetings.
• Qualify before you book — Apply a consistent set of qualification criteria so the meetings you book are genuinely worth the partners' time (see “What a Qualified Meeting Looks Like” below).
• Keep the CRM clean — Log every dial, conversation, disposition, and next step in the CRM so the pipeline is accurate and the partners walk into every meeting prepared.
• Hand off seamlessly — Smoothly transition qualified owners to the Managing Partners, including a clear written summary of the conversation, the owner's situation, and why they're a fit.
• Represent the brand and respect confidentiality.
• Hit your numbers and report on them — Track your own activity and conversion numbers, share what's working, and adjust messaging based on partner and market feedback.

Qualifications

Required:

• 1+ years in an SDR, BDR, inside sales, telemarketing, appointment-setting, or comparable high-volume phone role.
• Demonstrated comfort making 75–100+ calls per day and holding professional conversations with business owners and decision-makers.
• Hands-on experience with a dialer and/or CRM such as HubSpot or Outreach (or strong, fast aptitude to learn one).
• Clear, confident, articulate phone presence and the resilience to stay sharp through high call volume and rejection.
• Solid written communication for professional follow-up emails.
• Strong organization and CRM discipline — disciplined logging, follow-up, and pipeline hygiene.
• Self-motivated and accountable to clear daily activity and weekly booking targets in a remote environment.

Preferred:

• Experience selling or setting appointments for professional, financial, or advisory services.
• Exposure to M&A, business brokerage, commercial lending, insurance, or another consultative B2B sale.
• Familiarity with the trades, home services, landscaping, tree care, or other owner-operated industries.
• Experience with sales engagement / sequencing tools and basic familiarity with email deliverability best practices.

What's Offered

• A large, ready-to-work database — spend your time talking to owners, not building lists.
• A focused niche with a clear, repeatable pitch and real demand for what we do.
• Direct line to the Managing Partners, with coaching on messaging, objection handling, and qualification.
• Base salary plus commission tied to engagement letters signed.

If this sounds like a good fit, we'd love to hear from you!

Job Type: Full-time

Pay: $3,000,000.00 per month

Work Location: Remote