Sales Development Representative (SDR)

Weekday AI•San Francisco, CA

4d•$6,500,000 - $7,200,000•Onsite

About The Position

We are looking for an experienced and results-driven Sales Development Representative (SDR) to drive outbound pipeline generation and create new business opportunities within the mid-market segment. This role is ideal for a proactive sales professional who understands consultative prospecting, can engage senior decision-makers, and is comfortable owning the early stages of the sales cycle. As an SDR, you will be responsible for identifying high-potential prospects, researching target accounts, initiating meaningful conversations, qualifying opportunities, and creating a strong pipeline for the sales team. You will work closely with Account Executives and sales leadership to develop effective outbound strategies and convert targeted prospects into qualified opportunities. The ideal candidate combines strong communication skills with disciplined sales execution. You should be comfortable with high-volume and highly personalised outbound activities across email, phone, LinkedIn, and other prospecting channels. A strong understanding of mid-market buying processes, account research, objection handling, and lead qualification will be important for success.

Requirements

3+ years of experience in Sales Development, Business Development, Inside Sales, or a similar B2B sales role.
Strong hands-on experience in outbound prospecting and cold outreach.
Proven experience selling to or prospecting within the mid-market segment.
Demonstrated ability to generate qualified pipeline through outbound channels.
Excellent verbal and written communication skills.
Strong account research and prospecting abilities with a personalised approach to outreach.
Comfortable engaging with business leaders, decision-makers, and senior stakeholders.
Strong objection-handling, qualification, follow-up, and relationship-building skills.
Highly organised with excellent pipeline and activity management discipline.
Comfortable working with CRM and sales engagement tools.
Target-oriented mindset with a consistent track record of meeting or exceeding goals.
Self-motivated, resilient, and able to work effectively in a fast-paced sales environment.
Strong analytical mindset with the ability to use sales metrics to improve performance.

Responsibilities

Build and maintain a strong outbound pipeline across targeted mid-market accounts.
Research target companies, industries, business challenges, and key decision-makers.
Develop personalised outbound campaigns across email, phone, LinkedIn, and other channels.
Identify, engage, and qualify prospects based on defined business and opportunity criteria.
Conduct discovery conversations to understand prospect needs, challenges, priorities, and buying intent.
Schedule qualified meetings and create high-quality opportunities for Account Executives.
Follow up consistently with prospects throughout the qualification process.
Handle initial objections and communicate the value proposition effectively.
Maintain accurate prospect, activity, and opportunity information in CRM systems.
Track outbound performance and continuously improve conversion rates and messaging.
Collaborate with Account Executives, Sales Leadership, and Marketing to improve pipeline generation.
Monitor industry and account-level developments to identify relevant sales triggers.
Consistently achieve or exceed activity, meeting, pipeline, and revenue contribution targets.