Regional Vice President of Enterprise Sales, Observe.AI
Contact center software
Open for applications
Contact center software
201-500 employees
Open for applications
201-500 employees
Company mission
To enable brands to enhance their customer experience, with the power of contact center AI.
Role
Who you are
- 8–10+ years of B2B SaaS sales experience, including 3+ years in leadership managing mid-market or SMB teams
- Strong track record of net-new logo acquisition via outbound prospecting—personally and as a team leader
- Experience as a player-coach, balancing individual contributor responsibilities with team leadership
- Comfort building from scratch—people, processes, sales motions, and culture—in a high-growth or startup environment
- Familiarity with sales methodologies like MEDDIC, CCS, or Challenger, and tools like Salesforce, Outreach/Salesloft, Clari, Gong
- Strong storytelling and discovery skills; able to earn trust with technical and business stakeholders alike
Desirable
- Deep familiarity with GenAI, NLP, LLMs, or ML applications in enterprise use cases
- Global or multi-regional sales leadership experience (North America, EMEA, or APAC)
- Background in building high-performing sales teams at companies in post-Series B to pre-IPO stages
- Bachelor's or Master’s degree in Business, Engineering, or a related technical discipline
What the job involves
- We are hiring a Regional Vice President, Enterprise Sales to build and lead our outbound-led sales motion
- The RVP, Enterprise Sales will be at the forefront of driving new logo growth and engaging C-level executives across industries
- This is a hunter-first, player-coach role ideal for a high-energy leader who thrives in whitespace, has a track record of outbound pipeline generation, and is ready to build and lead a high-performing team
- You’ll be accountable for owning pipeline generation, closing new logos, and building the people, processes, and playbook to scale outbound-led revenue growth in the enterprise segment
- If you thrive in high-growth environments and are passionate about translating GenAI innovation into measurable customer outcomes, and shaping the future of customer experience - this role is for you
- Hunter Mentality & Outbound Strategy:
- Own and execute an outbound-first GTM motion targeting mid-market and enterprise accounts (typically <500 agents)
- Build and refine ICPs, persona-based messaging, outbound cadences, and prospecting strategies to drive predictable top-of-funnel activity
- Collaborate with marketing and SDR teams to align on high-converting campaigns
- Player-Coach Sales Leadership:
- Lead from the front as a quota-carrying seller, personally prospecting, engaging, and closing deals
- Hire, train, and coach a team of Mid-Market AEs, setting the tone for a metrics-driven, outbound culture
- Instill discipline around outbound KPIs—activities, pipeline coverage, conversion rates—while celebrating grit and curiosity
- Build & Scale the Function:
- Design the team structure, territories, compensation, hiring plan, and onboarding for an outbound-led mid-market motion
- Establish CRM best practices, forecasting cadences, pipeline review rituals, and enablement workflows
- Partner with RevOps, Product Marketing, and Enablement to iterate quickly based on data and feedback
- AI/GenAI Fluency:
- Understand and position the value of GenAI-powered solutions in contact center, CX, and revenue acceleration workflows
- Translate technical capabilities into business outcomes tailored for mid-market buyers across ops, support, and IT
- Stay ahead of GenAI trends, competitors, and evolving use cases in the customer engagement space
Our take
Being stuck on the phone to customer service can be time-consuming and frustrating. Observe.AI aims to improve the experience with its Intelligent Workforce Platform. This transforms contact centers through AI by automating tasks and form filling, helping people find more information quicker.
Unconventionally, the company gained its footing by going directly to the call centres themselves, rather than the businesses they serve - providing valued call optimization tools to improve operatives' performance. It also supplies an analysis engine for cross-channel customer interactions, which enables users to find new revenue opportunities, employ effective coaching and improve quality assurance.
Observe.AI has raised huge amounts of funding, demonstrating the high levels of confidence in its market position and performance. A major technological and commercial partnership with Zoom, alongside the growing trend in businesses prioritising customer interactions, bodes well for the company's future.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
3% employee growth in 12 months
Company
Funding (last 2 of 7 rounds)
Apr 2022
$125m
SERIES C
Sep 2020
$54m
SERIES B
Total funding: $223.2m
Company benefits
- Excellent medical, dental, and vision insurance options
- Flexible PTO
- Generous holiday (federal and wellness) recognition and parental leave policies
- 401K plan to save for your future
- Remote benefits including a daily meal stipend, WFH stipend, mobile & internet stipend to set you up for success in this remote environment
- Learning & Development fund to support you in your continuing education journey and professional development
- Fun events to build culture across the organization
Company HQ
Redwood Shores, Redwood City, CA
Leadership
Swapnil Jain
(Co-Founder & CEO)Previously completed an internship in Software Engineering at Google and worked at Twitter for 3 years, first as Senior Software Engineer and then as Technical Team Lead.
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