Who We Are?
We're GrowthSchool. And we built Outskill.
GrowthSchool started with one belief: you learn a skill fastest from the person actually doing it. So we partnered with the top 1% of instructors to build high-impact, cohort-based courses in personal and professional growth for learners around the world and used AI to make that learning personal at a scale a classroom never could.
Then AI changed what "upskilling" even means. Roles started getting rewritten faster than curriculums could keep up, and the real divide stopped being skilled versus unskilled. It became AI-ready versus not.
So, we built Outskill, our AI education arm, to close that gap, practical, implementation-first AI training for professionals, teams and enterprises. Today Outskill is one of the largest AI education companies in the world: 16M+ learners across 160+ countries, and programs running everywhere from individual upskilling to enterprise AI transformation.
Our mission: Make 100 million people AI-ready by 2028.
What that actually feels like day to day: we're 300+ people, backed by Sequoia, moving at a speed that surprises most people who join us. Products ship in weeks, not quarters. There's no thick layer of process between an idea and it going live. You'll own things visibly bigger than your title. Some experiments will fail publicly, and we'll talk about them openly on Monday.
If you need a finished playbook before you start, this will be uncomfortable. If you'd rather write the playbook, you'll like it here.
We're looking for a high-performing Enterprise Sales Manager / Senior Manager to own and scale our most strategic enterprise relationships. This role is responsible for driving end-to-end enterprise sales—from consultative discovery and solution design to commercial negotiations, deal closure, and long-term account growth.
You'll work with global organizations to solve complex workforce transformation challenges through AI-powered learning solutions. This role requires exceptional consultative selling skills, executive presence, and the ability to navigate complex, multi-stakeholder buying journeys while building trusted relationships with senior business leaders.
-
Own the complete enterprise sales cycle, including prospecting, discovery, solution consulting, commercial negotiations, contract closure, onboarding, and account growth.
-
Develop and execute winning sales strategies for large, multi-stakeholder enterprise opportunities.
-
Drive new business acquisition while expanding strategic customer relationships.
-
Partner with Product, Marketing, and Learning teams to design tailored enterprise solutions aligned with customer business objectives.
-
Lead executive presentations, solution demonstrations, RFP responses, proposals, and proof-of-concept engagements.
-
Translate complex customer requirements into compelling business cases and solution narratives.
-
Build trusted relationships with CXOs, CHROs, L&D leaders, HR teams, and Digital Transformation stakeholders.
-
Identify expansion opportunities through upselling, cross-selling, renewals, and long-term strategic partnerships.
-
Conduct regular business reviews and proactively drive customer success and account health.
-
Manage enterprise customers across international markets and navigate global procurement, legal, commercial, and operational processes.
-
Serve as the primary relationship owner for strategic global accounts.
-
Build strong relationships across multiple stakeholders, business units, and geographies.
-
Own individual revenue targets and maintain a healthy enterprise sales pipeline.
-
Build accurate forecasts and provide regular pipeline updates to leadership.
-
Apply structured deal qualification methodologies to maximize conversion rates and sales efficiency.
-
Ensure CRM accuracy and maintain strong sales process discipline.
-
Monitor market trends, customer needs, competitor activities, and industry developments.
-
Share customer insights with Product, Marketing, and Leadership to strengthen go-to-market strategy.
-
Act as the voice of the enterprise customer and contribute to product positioning and roadmap discussions.
We're looking for a consultative enterprise sales professional who thrives in complex sales environments and enjoys building long-term strategic relationships. The ideal candidate combines strong commercial acumen with executive presence, solution-selling expertise, and the ability to influence senior decision-makers across global organizations.
-
6+ years of experience in Enterprise Sales or B2B Sales with end-to-end ownership of complex sales cycles.
-
Proven track record of closing high-value enterprise deals with mid-to-large organizations.
-
Strong experience in both new business development (hunting) and account growth (farming).
-
Experience managing consultative sales engagements, including solution design, negotiations, and executive presentations.
-
Strong stakeholder management skills with the ability to engage CXOs, CHROs, HR leaders, Procurement, and L&D decision-makers.
-
Experience managing enterprise pipelines, forecasting, CRM systems, and revenue reporting.
-
Excellent communication, presentation, negotiation, and consultative selling skills.
-
Strong commercial mindset with the ability to manage multiple complex opportunities simultaneously.
-
Ability to work independently in a fast-paced, high-growth environment.
-
Experience selling SaaS, AI, HRTech, EdTech, Learning & Development, or Digital Transformation solutions.
-
Experience managing international enterprise accounts across APAC, US, UK, or Middle East markets.
-
Familiarity with enterprise procurement processes, contract negotiations, and long sales cycles.
-
MBA from a leading business school (IIM, ISB, or equivalent).
-
Understanding of AI, GenAI, enterprise learning platforms, or workforce transformation solutions.
-
Opportunity to work with some of the world's leading enterprises on AI transformation initiatives.
-
Ownership of strategic, high-value enterprise accounts with direct business impact.
-
A high-performance, entrepreneurial culture with significant autonomy and ownership.
-
Competitive compensation with attractive performance-based incentives.
-
Direct collaboration with founders and senior leadership on enterprise growth strategy.
-
Strong opportunities for career progression and leadership development.
Hyderabad, India
