Head of Sales
About the job
- At least 8 years of sales experience, including a minimum of 2 years of leadership experience managing a sales function and team.
- Proven success closing complex, high-value software-as-a-service deals and building repeatable sales motions.
- Strong executive-level selling skills and the ability to navigate multiple stakeholders and long sales cycles.
- Ability to work cross-functionally with Marketing, Product, Customer Success, and Sales Operations.
- Experience using metrics and forecasting to guide decision-making.
- Passion for technology, especially artificial intelligence, and the ability to clearly articulate value and return on investment to customers.
- Prior experience helping scale a high-growth startup, with comfort operating in ambiguity.
- Own and lead end-to-end sales strategy and execution across all customer segments.
- Manage and optimize the full sales process from pipeline generation through close.
- Partner with Marketing, Product, Engineering, and Customer Success to align go-to-market strategy and deliver customer outcomes.
- Drive consistent and accurate sales forecasting and pipeline visibility.
- Identify opportunities to accelerate revenue growth through improved positioning, pricing, packaging, and sales process improvements.
- Hire, develop, and performance-manage a high-caliber team of Account Executives.
- Establish scalable sales playbooks, metrics, and operating rhythms as the team grows.
- Act as the voice of the customer by bringing market insights to product and leadership teams.
About the company
Regal provides outbound customer outreach tools for contact centers. It turns existing customer data into personalized, multi-channel campaigns across phone, SMS, email, chat, and AI-driven agents to drive conversations that convert and increase revenue. The system analyzes untapped data to identify the best contact and the best moment to reach them, enabling agents to engage at the right time with tailored messages. Regal differentiates itself by promising a clear, measurable lift—25% more revenue—through a unified, omnichannel approach that combines human interactions with AI-enabled messaging. Its goal is to help contact centers maximize revenue potential by delivering relevant, timely, and consistent outreach across all channels.
Company Size
51-200
Company Stage
N/A
Total Funding
N/A
Headquarters
New York City, New York
Founded
2020
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Simplify's Take
What believers are saying
- October 2024's $40 million round gave Regal capital to scale AI Phone Agents.
- Regal's 2026 product cadence shows rapid shipping across MCP, observability, and CCaaS.
- The Five9 channel can accelerate enterprise deal flow in regulated contact centers.
What critics are saying
- Five9, Genesys, and Twilio can bundle similar AI orchestration, crushing Regal margins.
- Regal's enterprise pitch depends on integrations; one platform change can break distribution.
- Voice AI failures, hallucinations, or compliance incidents can trigger buyer freezes and existential churn.
What makes Regal unique
- Regal's August 2026 Five9 integration embeds AI agents inside enterprise workflows.
- Regal's April 2026 Copilot automates building, testing, monitoring, and improving AI agents.
- Regal serves 200+ enterprises across phone, SMS, email, chat, and AI agents.
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Benefits
- Health Insurance
- Dental Insurance
- Vision Insurance
- 401(k) Retirement Plan
- Paid Parental Leave
- Pre-tax Commuter Benefits
- Paid Holidays