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Reports to: Director of Sales

About Milestone 

Milestone is the AI-native digital experience platform that makes brands discoverable in AI search. Milestone helps brands measure their visibility across ChatGPT, Gemini, AI Overviews, Perplexity, and Claude, optimize content for AI discovery, and build AI-first websites with agent-ready infrastructure that turns AI discovery into direct bookings and higher conversions. Founded in 1997 and headquartered in Silicon Valley, Milestone powers 5,000+ websites for leading brands in hospitality, financial services, retail, automotive, and healthcare. Learn more at www.milestoneinternet.com.

Position Summary

The Sales Development Representative (SDR) is responsible for generating qualified pipeline within the Financial Services and Hospitality segments. This is a quota-carrying prospecting role focused on identifying, engaging, and qualifying new prospects, setting and completing discovery meetings, and partnering with Opportunity Owners to advance qualified opportunities through proposal to close. The SDR is the first point of contact for prospective clients and plays a direct role in the growth of the business.

Performance Expectation:

This role carries the following monthly performance standards, consistent with the team-wide SDR standard:

Metric	Monthly Target	Definition
Meeting Completes (MC)	7 per calendar month	A meeting with a Financial Services or Hospitality prospect where the SDR is the Pre-Qualified By owner in the CRM and the meeting is marked completed.
Proposal Conversations	3 per calendar month	A qualified opportunity advanced to an active proposal discussion with the assigned Opportunity Owner.
Deal Wins	1 per calendar month	A closed-won opportunity originated by the SDR and credited per the current compensation plan.

Performance against these metrics is reviewed monthly. Each calendar month is measured independently, with results counted in the month the activity occurred.

Key Responsibilities:

• Prospect into target accounts within the Financial Services and Hospitality segments through outbound calling, email, and social outreach.
• Identify and qualify prospect needs, budget, and decision-making structure to determine fit before advancing an opportunity.
• Schedule, confirm, and complete discovery meetings, achieving the monthly meeting-complete standard.
• Partner with Opportunity Owners to advance qualified opportunities into proposal conversations and through to close.
• Build and maintain a written weekly target account list, including ICP alignment, contact mapping, and outreach sequencing.
• Log all prospecting activity in the CRM accurately and on the same business day, and maintain current records on all active opportunities.
• Distribute outreach consistently across the business week rather than concentrating activity into a small number of days.
• Participate actively in weekly 1:1s, pipeline reviews, and call coaching sessions, applying feedback week over week.
• Communicate blockers, territory questions, and process issues promptly and in writing.

Activity Standards:

• Prospecting activity logged in the CRM by 5:00pm local time each business day.
• Activity spread across all five business days each week (absent PTO), with no single day exceeding 50% of that week's total call volume.
• Planned PTO submitted at least 14 calendar days in advance where possible.

Required Qualifications:

• 1-2 years of experience in an outbound sales, sales development, business development, or comparable customer-facing role.
• Demonstrated success working to a measurable activity or pipeline quota.
• Strong verbal and written communication skills, with comfort in high-volume phone outreach and cold conversations.
• Working proficiency with a CRM and standard sales productivity tools.
• Consistent, self-directed daily discipline and effective time management.
• Coachability — willingness to receive feedback and apply it quickly.

Preferred:

• Experience selling into Financial Services (banks, credit unions) or Hospitality/Lodging.
• Familiarity with multi-touch outbound sequencing and account-based prospecting methods.
• Bachelor's degree or equivalent practical experience.

Success in first 90 days:

• Days 1-30: Complete onboarding and product training, build an initial target account list, and begin consistent daily outbound activity.
• Days 31-60: Achieve full activity standards and begin producing completed meetings against the monthly standard.
• Days 61-90: Perform at the full monthly standard of 7 meeting completes, 3 proposal conversations, and 1 deal win.

Why Milestone? 

AI is transforming how customers discover and choose brands, and Milestone has spent nearly three decades helping enterprises win the moments that matter, first in search, now in AI search. You'll define that future while building the marketing engine for a profitable, established platform trusted by some of the biggest names in hospitality and beyond. If you enjoy turning ideas into impact, building a respected brand, and working alongside a fast-moving leadership team, we'd love to meet you.