Obsidian Systems LLC · 1 month ago
Head of Sales (Financial Enterprise)
United States
Full-time
Remote
Director/Executive
8+ years expObsidian Systems LLC is a founder-led consulting and engineering firm focused on building complex systems for traditional finance. They are seeking a Head of Sales to transition their sales approach while maintaining a high-trust culture, involving hands-on sales leadership and relationship management with large financial institutions.
Information TechnologyRoboticsSoftware
Responsibilities
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
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
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
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
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
Qualification
Required
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
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
Company
Obsidian Systems LLC
Obsidian Systems designs and develops high quality software solutions to pressing business problems.
11-50 employees
H1B Sponsorship
Obsidian Systems LLC has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (2)
2024 (8)
2023 (6)
2022 (16)
2021 (9)
2020 (8)
Funding
Current Stage
Early StageLeadership Team
Ryan Trinkle
Partner
Company data provided by crunchbase