Outbound Sales Representative

About LeadWire LeadWire is a revenue-activation platform that is redefining how brands communicate with their customers through text and multimedia messaging. Headquartered in San Juan, Puerto Rico, our mission is to help companies create real-time connections that drive measurable results. Our platform is used by brands across industries to send millions of personalized messages monthly — from promotions and campaigns to operational updates — enabling them to activate their audience instantly and build owned communication channels. We are currently in a rapid growth phase and focused on scaling our revenue operations across multiple markets. This is a unique opportunity to join a fast-growing SaaS company at a critical stage and play a direct role in its expansion. Position Overview LeadWire is looking for an Outbound Sales Representative to support our pipeline generation efforts and help scale our outbound motion. You will play a key role in identifying, engaging, and qualifying potential customers, working directly with the leadership team in a fast-paced startup environment. This role operates within a structured sales process designed to generate qualified pipeline and support overall business growth. What you’ll do Identify and research target accounts aligned with LeadWire’s ideal customer profile Execute high-volume, high-quality outbound prospecting across three channels: cold calls, personalized emails, and LinkedIn Engage with prospects to understand their business needs, challenges, and objectives, and effectively communicate the value proposition of our product. Generate and qualify conversations with potential customers Book meetings with qualified prospects Maintain accurate records and pipeline activity in HubSpot Follow structured outreach sequences and qualification frameworks Collaborate with internal teams to improve messaging and targeting Contribute to building a consistent pipeline of qualified opportunities Work closely with marketing to provide feedback on lead quality and campaign effectiveness, and leverage marketing materials to support outreach efforts. Collaborate closely with Sales Team on handoffs, ensuring warm context transfer so no momentum is lost Preferred skills and qualifications Bachelor’s degree (or equivalent) in business, marketing, or related field 1–3+ years of experience in sales, marketing, or a related role Strong communication skills (written and verbal) High level of organization and attention to detail Ability to work independently and manage multiple priorities Comfort with outbound outreach and fast-paced environments Interest in sales, marketing, and business growth Familiarity with CRM tools (HubSpot preferred) Why join LeadWire Be part of a high-growth SaaS company Work closely with leadership on high-impact initiatives Gain exposure to sales strategy and revenue operations Opportunity to make a direct impact on company growth