Enterprise Account Executive ($150k-$300k + Equity) at Uncork Capital-backed cloud cost SaaS startup
Jack & Jill · San Francisco, CA
- On site
- Full-time
- $225,000 / year
- San Francisco, CA
Job highlights
- Own enterprise SaaS sales cycle for cloud cost management.
- Leverage strong market authority and existing customer network.
- Collaborate with founders on product development.
- Requires 2-3 years of AE experience.
- Ideal for technically curious, AI-native professionals.
About the role
Enterprise Account Executive
Join a high-growth cloud cost management leader transitioning from boutique advisory to a powerful SaaS platform, Skyway. You will own the full sales cycle for enterprise cloud and AI financial tools. Inherit a trusted brand with 35,000+ newsletter subscribers and active demand while building scalable strategies for the AI-native economy.
About Skyway
Uncork Capital-backed SaaS startup managing $10B+ in cloud spend for the Fortune 500.
Why this role is remarkable
- Market Authority: Leverage a massive existing footprint including 5 million podcast downloads and 100k+ followers, ensuring you never walk into a cold room.
- Proven Traction: Backed by Heavybit and Uncork Capital with $7.75M raised and a track record of negotiating tens-of-billions in cloud contracts.
- AI-Forward Culture: Direct impact on a product solving the urgent complexity of Anthropic, OpenAI, and AWS commitments for world-class engineering teams.
What You Will Do
- Own the full sales cycle from initial qualification and deep discovery through to managing complex stakeholder groups and closing high-value deals.
- Proactively build a robust pipeline by re-engaging the firm's extensive customer network, referral channels, and outbound efforts alongside consistent inbound interest.
- Collaborate directly with founders and technical teams to translate customer pain points into platform features for the newly launched Skyway product.
The ideal candidate
- Proven closer with 2-3 years of AE experience, ideally with a background in high-volume SDR roles and a desire for true book ownership.
- Technically curious professional who thrives in ambiguity and can navigate decentralized buying groups across engineering, finance, and infrastructure departments.
- AI-native worker who actively utilizes AI tools for research and productivity, with the discipline to maintain accurate CRM data in HubSpot.
Key skills/competency
- Enterprise Account Executive
- SaaS Sales
- Cloud Cost Management
- AI Financial Tools
- Full Sales Cycle Ownership
- Pipeline Building
- Customer Relationship Management (CRM)
- HubSpot
- Enterprise Software Sales
- Fortune 500 Sales
Skills & topics
- Enterprise Account Executive
- SaaS Sales
- Cloud Cost Management
- AI Financial Tools
- Sales Cycle
- Pipeline Management
- HubSpot CRM
- Enterprise Software
- Fortune 500
- Account Executive
How to get hired
- Customize your resume: Highlight your 2-3 years of AE experience and any SDR background, emphasizing book ownership and deal-closing success.
- Showcase technical curiosity: Detail your experience navigating complex buying groups and using AI tools for research and productivity.
- Tailor your application: Explicitly mention your familiarity with HubSpot CRM and your understanding of cloud cost management or AI financial tools.
- Prepare for interviews: Be ready to discuss your experience managing the full sales cycle and how you build robust pipelines through various channels.
- Engage with Jack & Jill: Understand their unique recruitment process and how Jack can help facilitate your introduction to the hiring team.
Technical preparation
Master SaaS sales methodologies and CRM usage.,Understand cloud cost management and AI financial tools.,Practice navigating complex enterprise buying groups.,Develop proficiency with AI research and productivity tools.
Behavioral questions
Describe a complex deal you closed.,How do you build and manage a sales pipeline?,How do you collaborate with technical teams?,How do you stay updated on AI advancements?
Frequently asked questions
- What is the typical career path for an Enterprise Account Executive at Skyway?
- As an Enterprise Account Executive at Skyway, you'll have the opportunity to own the full sales cycle and directly impact product development. With 2-3 years of experience, you're positioned for significant growth within this high-growth SaaS startup, potentially leading to senior sales roles as the company expands. Your success in closing high-value deals and collaborating with founders will be key to advancing your career.
- How does the AI-driven recruitment process with Jack & Jill work for this Enterprise Account Executive role?
- Jack & Jill use a unique AI-driven process. Jack, your AI career coach, gets to know you and helps you find opportunities. Jill, the AI recruiter, identifies suitable candidates from Jack's network for her clients. If there's a match for the Enterprise Account Executive position, Jill will facilitate an introduction to the hiring company. It's a direct line to a real job opening.
- What kind of technical curiosity is expected for the Enterprise Account Executive position?
- For this Enterprise Account Executive role, technical curiosity means being able to navigate complex buying groups that include engineering, finance, and infrastructure departments. You should be comfortable discussing AI financial tools and cloud cost management solutions. The ideal candidate actively uses AI tools for productivity and research, demonstrating an innate understanding of the AI-native economy.
- How important is AI tool usage for an Enterprise Account Executive at this company?
- Being an 'AI-native worker' is a key characteristic for this Enterprise Account Executive role. The company is at the forefront of AI financial tools and cloud cost management. Actively utilizing AI tools for research and productivity is expected, alongside maintaining accurate CRM data. This demonstrates your adaptability and forward-thinking approach in the AI-native economy.
- What are the expectations regarding CRM data accuracy for an Enterprise Account Executive?
- Maintaining accurate CRM data, specifically in HubSpot, is crucial for the Enterprise Account Executive role. This discipline ensures that the extensive customer network and referral channels can be effectively managed and re-engaged for pipeline building. Accurate data allows for targeted outreach and informed collaboration with founders and technical teams.
- How does Skyway leverage its existing market authority for the Enterprise Account Executive role?
Similar roles
Open positions we recommend based on this role.