Sales Development Representative at Pinewood.AI

Description

As a Sales Development Representative (SDR), you will be responsible for generating and qualifying new sales opportunities for Pinewood.AI’s Dealer Management System (DMS) and Seez’s AI-powered solutions. This is a front-line, outbound-focused role that supports a pure hunter enterprise sales team.

You will prospect into large dealership groups, engage senior dealership leaders, qualify complex opportunities, and set high-quality meetings for Enterprise Sales Representatives. Success in this role requires persistence, curiosity, strong communication skills, and comfort initiating conversations around platform-level change.

Key Responsibilities

• Prospect and generate new opportunities for Pinewood.AI DMS and Seez AI solutions
• Execute outbound outreach through cold calls, email, and social channels
• Respond to and qualify inbound leads against defined ICP and buying criteria
• Engage dealership principals, GMs, IT leaders, and digital decision-makers
• Qualify prospects and schedule discovery calls and demos for Enterprise Sales
• Research target dealership groups and identify buying signals
• Maintain accurate activity, notes, and opportunity data in the CRM
• Meet or exceed monthly activity, pipeline, and qualified meeting targets
• Partner with marketing to support outbound campaigns and account-based efforts
• Share prospect feedback, objections, and market insights with sales leadership
• Support the sales team at industry events and trade shows as needed

Requirements

• 2+ years of experience in B2B sales development, inside sales, or similar role
• Proven success in outbound prospecting and pipeline generation
• Strong verbal and written communication skills
• Confident phone presence and ability to engage senior decision-makers
• Experience using CRM and sales engagement tools (Microsoft Dynamics, etc.)
• Bachelor’s degree or equivalent experience preferred
• Comfortable working in a fast-paced, metrics-driven environment

Desired Skills & Attributes

• Familiarity with automotive retail or dealership operations
• Experience selling SaaS or enterprise technology
• Strong qualification and discovery skills
• Resilient, competitive, and comfortable handling rejection
• Highly organized with strong attention to detail
• Self-motivated with a clear desire to advance into an Enterprise Sales role

Why Join Pinewood.AI?

Pinewood.AI is a global automotive technology company using data and AI to help dealers operate better, sell more, and deliver stronger customer experiences. Our platform supports sales, service, and dealership operations while working alongside existing systems.

With the recent acquisition of Seez, a leader in AI-powered automotive retail solutions, Pinewood.AI is scaling quickly. Seez’s proven AI technology and international success, combined with Pinewood.AI’s deep industry footprint, are fueling our expansion in the U.S., including a strategic partnership with Lithia Group, one of North America’s largest dealership networks.

We’re building a team to shape the future of automotive retail and are looking for people who want to make a real impact as we grow.

About Us

Our story began more than 20 years ago with a clear purpose to create technology designed around the real needs of automotive retailers. As automotive professionals as well as technologists, we built practical solutions that help dealerships run more efficiently and deliver outstanding customer experiences. 

Today, Pinewood.AI is a market leader in dealership management and automotive intelligence. Our cloud-based platform connects every part of a retailer’s business, including vehicle sales, service, parts, workshop, finance, insurance, stock management, customer relationship management, and business reporting. By bringing everything together in one intelligent system, we help retailers and manufacturers make better decisions, improve performance, and increase profitability. 

We are now expanding into North America, bringing our proven platform to a new audience. This is an important stage in our growth where we are building our presence in the United States and Canada. Joining Pinewood.AI at this time means becoming part of a fast-growing, startup-style team that is supported by an established and successful global business. You will play a key role in introducing and embedding our platform across North American dealerships. 

Benefits

• A very competitive salary plus commission structure
• Flexible mix of home and office working 
• Clear path to Enterprise Sales for top performers

• 4 weeks PTO 

• 401k 
• Excellent health insurance benefits

• Regular 1-2-1s and career development opportunities
• Opportunity to be part of an early-stage US sales team with real ownership