Helpware is a people-first outsourcing and customer experience partner helping fast-growing companies scale support, operations, and revenue teams with AI-enabled CX solutions. We work with SaaS, Fintech, Healthcare, Ecommerce, and Logistics brands across the US, UK, and beyond.
We're hiring a Sales Development Representative to support outbound sales and build qualified pipeline for our Account Executive team. This role is for someone hungry, coachable, and ready to build a real sales career with structured onboarding, hands-on coaching, and earning upside tied directly to your performance. You'll have the tools, training, and support you need to learn fast and deliver results.
What you'll do
- Cold outreach — make outbound calls to prospective clients across Helpware's target verticals (SaaS, Fintech, Healthcare, Ecommerce, Logistics) using Genesys
- Email & LinkedIn — execute pre-built email sequences in HubSpot and run LinkedIn touches alongside your calls for full multi-channel coverage
- Prospect research — research target accounts and decision-makers using LinkedIn, Apollo, ZoomInfo, and our CRM data
- Lead qualification — qualify outbound leads against target criteria using the team's discovery framework, identify pain points, and handle objections professionally
- Meeting bookings — schedule qualified discovery calls for Account Executives with confirmed prospects and complete handoff context
- CRM management — keep HubSpot records accurate and up-to-date; document every conversation, follow-up, and next step
- Hit your activity targets — meet weekly and monthly KPIs on calls, emails, sequence enrollment, and meetings booked
- Collaborate & improve — share what you're hearing on calls with Sales Enablement, RevOps, and Marketing so we can sharpen scripts, sequences, and targeting together
What you bring
- At least 1 year of experience in sales, sales development, lead generation, appointment setting, or B2B/B2C outbound—or strong customer-facing experience (CSR, retention, telemarketing) with a clear commitment to building a sales career
- Good verbal and written English — comfortable speaking with US, UK, and Australian prospects on the phone and via email
- Phone confidence — willing and able to make high volumes of outbound calls and stay resilient through rejection
- Coachability — open to feedback, eager to be coached, willing to practice scripts and role-play until they're sharp
- Organized and self-motivated — can manage your own follow-ups, prioritize your day, and stay on top of multiple prospects simultaneously
- Goal-oriented mindset — you want to hit targets, not just do activity for its own sake
- Basic CRM familiarity — exposure to HubSpot, Salesforce, GoHighLevel, or similar platforms is a plus (we'll train you on our stack)
Nice to have
- Exposure to selling BPO, customer support, AI-enabled services, or SaaS
- Familiarity with LinkedIn Sales Navigator, Apollo, ZoomInfo, or similar prospecting tools
- Experience supporting US-based clients on night-shift schedules
- Basic understanding of B2B sales processes and pipeline management
Skills Required
- At least 1 year of experience in sales or customer-facing roles
- Good verbal and written English communication skills
- Confidence in making outbound calls
- Ability to accept feedback and improve
- Organizational skills to manage follow-ups and prospects
- Goal-oriented with a focus on hitting targets
What We Do
Founded in 2015, Helpware is a company taking a modern approach to the outsourcing industry. We created the company to change perceptions of what outsourcing is and can be, and we did that by building amazing cultures in each of our locations, and by simply treating our employees better. With Helpware, we are all a team and family, and you'll see that true difference when partnering with us. Helpware builds customized teams in Customer Service and Back Office for industry-leading startups and modern companies. With offices in California, Colorado, Kentucky, Ukraine, Philippines, Germany, and Mexico, we have the global scale to tailor custom teams and processes for success to our many powerhouse clients. Helpware has grown over the years, initially catering to startup client partners, and has now evolved into creating client partnerships with large enterprises as well.
