Senior Sales Development Representative

Why this role

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 Senior SDR to drive outbound pipeline into mid-market and enterprise accounts. You'll lead a focused outbound team by running multi-channel campaigns, qualifying decision-makers, and producing high-quality opportunities for our Account Executive team. This senior, full-cycle prospecting role offers strong earning potential, modern tools, and direct partnership with Sales Leadership and Revenue Operations.

What you'll own

Pipeline generation — own outbound prospecting strategy and execution for mid-market and enterprise accounts across Helpware's target verticals (SaaS, Fintech, Healthcare, Ecommerce, Logistics)

Multi-channel outreach — manage cold calling with Genesys, email sequencing with HubSpot, and LinkedIn outreach in coordinated, ICP-targeted campaigns

Qualification — run structured discovery calls with decision-makers, document qualification thoroughly, and identify business pain points worth pursuing for Helpware

Account research — develop deep account intelligence on enterprise prospects, decision-makers, and buying committees

Opportunity handoff — book qualified discovery meetings for Account Executives with complete context and clear next-step plans

Campaign optimization — collaborate with RevOps, Sales Enablement, and Marketing on A/B-tested scripts, sequences, and playbook variants

Performance ownership — meet weekly and monthly activity KPIs while maintaining high conversation quality and CRM hygiene

What you bring

3+ years of B2B outbound sales experience — SDR, BDR, lead generation, appointment setting, or similar (exceptional candidates with 2-year and proven track records will be considered)

Excellent verbal and written English — comfortable engaging C-level, VP, and Director-level decision-makers at US, Canadian, UK, and Australian companies

Confident phone presence — comfortable with cold outreach, professional objection handling, and consultative selling under sales pressure

CRM fluency — strong working knowledge of HubSpot (preferred) or comparable platforms (Salesforce, GoHighLevel); experience maintaining accurate pipeline data and using sales engagement tools

Prospecting tool experience — familiarity with LinkedIn Sales Navigator, Apollo, ZoomInfo, or similar B2B intelligence platforms

Self-directed work ethic — comfortable managing your pipeline, prioritizing high-value accounts, and working independently in a remote setting

Track record of meeting quota — references or documented performance showing consistent achievement of activity and pipeline targets

Nice to have

Experience selling BPO, customer support, CX outsourcing, AI-enabled services, or SaaS to North American buyers

Background in account-based outbound prospecting against named enterprise account lists

Familiarity with outbound sequence design and A/B testing principles

Prior experience on US-aligned night-shift schedules