[Hiring] Enterprise Solutions Strategist @Flipside Crypto

Role Description

We're looking for someone to work directly with the CEO to build enterprise relationships and close deals. This is not a quota-carrying AE role. It's closer to a founding GTM partner - someone with high EQ, creative deal instincts, and the ability to navigate complex organizations and build trust at multiple levels.

What You'll Actually Do

• Work the enterprise deal cycle alongside the CEO
• Own the mechanics: discovery prep, proposal drafting, SOW structuring, contract navigation, procurement sequencing
• Help shape positioning for each account - this is consultative selling, not product selling
• Keep deals moving; know where each opportunity stands and what it needs next
• Translate between our engineering team and the business
• Participate in technical discovery sessions; understand what our solutions actually do, then help package it into commercial proposals and SOWs that make sense
• Work with our CTO and data science leads to scope what's deliverable, at what margin, on what timeline
• Build the playbook as we go
• Develop repeatable engagement models - from POC to expansion SOW to subscription - that we can run across multiple accounts simultaneously
• Think in deal economics: services vs. software mix, margin targets, expansion triggers, long-term account value
• Build templates and frameworks so that enterprise sales becomes a system, not a series of heroic one-offs
• Own your relationships
• Represent edisyl at industry events and in direct outreach
• Manage the rhythm of communication so the CEO's time is preserved for highest-leverage moments

What Success Looks Like in Year One

• By the end of year one, you've closed two to three enterprise deals, each with a named champion you cultivated - not inherited.
• You've documented a playbook someone else could follow, and you've built a pipeline that reflects real relationships, not just names in a CRM.
• The measure isn't just revenue - it's whether the enterprise motion is a real, repeatable thing that exists because you built it.
• You'll know you're winning when the deals you're running have genuine momentum behind them, the champions in your accounts are calling you, and the CEO stops having to carry the deal mechanics and shows up only at the moments that need them.

Qualifications

• 4–8 years in a role that combined enterprise selling with technical understanding: enterprise sales at a data or AI company, solutions engineering, technical account management, or consulting with a hard pivot into tech
• Experience close to six-figure-plus deals; familiarity with MSAs, SOWs, security reviews, and multi-stakeholder approval chains
• Understanding of data and AI well enough to talk intelligently about pipelines, models, agents, and infrastructure

Requirements

• High EQ: ability to read rooms, adjust your register, and build trust with skeptics
• Creative deal instinct: ability to shape engagements around problems
• Written clarity: ability to write proposals, SOWs, and deal memos that people actually read
• Organized without being reminded: ability to build systems for tracking and follow-up
• Low ego, high agency: comfortable with whatever the deal needs on any given day
• AI-native: stay close to how these tools are evolving and use them

Bonus (Genuinely Not Required)

• Background at Palantir, Databricks, Snowflake, or another company running a forward-deployed or consultative sales model
• Management consulting with a move into enterprise tech
• Experience working directly with a CEO or founder in a small-company environment
• Familiarity with blockchain data, DeFi, or institutional crypto

Compensation

• Competitive base salary
• Meaningful early-stage equity
• Variable component tied directly to the deals you close

To Apply

Send an email to [email protected] with two things: 1) why this role fits where you are in your career right now, and why you are the best for the role; and 2) one example of a complex deal or engagement you helped drive to close. No cover letter template. Just tell us the story.