AI-Driven SDR | Pipeline Builder for FinServ & Hospitality

Milestone Inc.; Palo Alto (CA); On-site; USD 75,000 - 110,000; Full time

Job summary

Milestone is seeking a Sales Development Representative (SDR) to generate qualified pipeline within Financial Services and Hospitality. You will be the first contact for prospective clients and will prospect via outbound calls, emails, and social outreach, qualifying needs to hand off to Opportunity Owners.

This quota-carrying role requires disciplined daily activity, accurate CRM logging, and strong collaboration with the sales team to move opportunities from discovery to close.

Qualifications

• 1–2 years of outbound sales experience in a customer-facing role.
• Proven ability to meet activity or pipeline quotas.
• Excellent verbal and written communication skills.
• Experience with CRM and standard sales productivity tools.
• Self-directed daily discipline and effective time management.
• Coachability and quick adoption of feedback.

Responsibilities

• Prospect into target accounts within Financial Services and Hospitality 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.

Skills

Outbound sales

CRM proficiency

Strong communication

Time management

Coachability

Written communication

Education

Bachelor's degree or equivalent

Tools

CRM

Job description

Milestone is seeking a Sales Development Representative (SDR) to generate qualified pipeline within Financial Services and Hospitality. You will be the first contact for prospective clients and will prospect via outbound calls, emails, and social outreach, qualifying needs to hand off to Opportunity Owners.

This quota-carrying role requires disciplined daily activity, accurate CRM logging, and strong collaboration with the sales team to move opportunities from discovery to close.