Head of Sales (Financial Enterprise)

Obsidian Systems

12h

About The Position

Obsidian is a founder-led consulting and engineering firm of ~40 senior software engineers building complex systems for some of the most sophisticated institutions in traditional finance. We are hiring our first Head of Sales to help us transition from founder-driven selling to a repeatable, institutionally credible sales motion—without losing our scrappy, high-trust, high-judgment culture. This role is intentionally designed for someone who fits ~70% of a classic enterprise Head of Sales profile. You do not need to have built a 50-person sales org, owned a global quota, or worked inside a fully mature revenue machine. You do need to be: Comfortable selling into large, regulated financial institutions Credible with senior stakeholders at banks and financial infrastructure firms Willing and able to do the work yourself while helping founders level up the motion This role is: Hands-on Founder-adjacent Relationship-driven Built for a small, elite engineering organization This role is not: A late-stage CRO role A pure crypto-native BD or ecosystem role A heavily resourced, top-down sales org build If you want to help a technically exceptional team win and expand relationships with some of the most demanding institutions in finance—this role is for you. This role may be full-time or fractional for the right person.

Requirements

8+ years in enterprise sales, business development, or partnerships within financial services, fintech, capital markets, or enterprise technology.
Experience selling complex, technical consulting or software solutions into large organizations.
An existing network of relationships across banks, custodians, asset managers, trading firms, or financial infrastructure providers.
Comfortable operating without a mature sales org, enablement team, or playbooks.
Pragmatic, low-ego, and willing to roll up your sleeves.
Able to give founders strong guidance while respecting a founder-led culture.

Responsibilities

Founder-Adjacent Sales Leadership
Partner directly with Obsidian’s founders to evolve our sales approach from founder-led to founder-supported.
Provide guidance, structure, and pattern recognition—without imposing heavyweight enterprise bureaucracy.
Help founders decide where to lean in personally and where sales can (and should) run independently.
Hands-On Enterprise Selling
Personally originate, develop, and close consulting engagements with large financial institutions, market infrastructure providers, and regulated digital asset firms.
Leverage existing institutional relationships to create qualified, high-trust entry points.
Lead discovery conversations with executive, business, and technical stakeholders.
Translate complex engineering capabilities into clear business value, risk mitigation, and ROI narratives.
Lightweight Process & Signal Creation
Design just enough sales process to create visibility and momentum: pipeline stages, deal notes, forecasts, and clear next steps.
Help implement early tooling (CRM, basic reporting) appropriate for a small but growing firm.
Establish shared language around qualification, scoping, and deal health.
Scoping, Pricing & Closing
Partner with founders and technical leaders to scope engagements that are realistic, profitable, and delivery-ready.
Support proposal development, pricing conversations, and contract negotiation.
Navigate enterprise procurement, legal, and compliance processes pragmatically—not theoretically.
Internal Alignment
Work closely with consulting and engineering leadership to ensure sales commitments align with delivery capacity.
Act as a bridge between institutional clients and a deeply technical delivery team.