Director, Strategic Sales
Job description
About the role
This position defines and owns strategic sales initiatives for Tailscale within the United States market, shaping how the company wins and retains large customers. The hire will be responsible for discovering complex business problems and translating them into Tailscale value propositions that resonate at the executive level. They will build and maintain executive-level relationships that position Tailscale as core networking infrastructure for critical workloads and long-term digital transformation. The role requires owning the end-to-end strategic sales cycle, driving new business revenue for strategic accounts from initial discovery through contract negotiation and expansion. Success in this role depends on the ability to quantify customer business problems and tailor Tailscale solutions to align precisely with enterprise buying criteria and procurement processes. The hire will collaborate closely with product and engineering teams to incorporate market feedback into Tailscale product direction and to design, then validate, sales playbooks that scale across strategic accounts. Pipeline and conversion metrics will directly translate into forecast accuracy and revenue targets that the hire is accountable for meeting on a quarterly and annual basis. This is a quota-driven role where consistent activity, honest qualification of deals, and disciplined follow-through are essential for achieving success.
Key facts
What you'll do
Execute the end-to-end strategic sales cycle, from discovery through contract negotiation and expansion, to drive new business revenue for strategic accounts.
Position Tailscale solutions as core networking infrastructure that solves customer business problems and builds executive-level relationships for critical workloads.
Quantify customer business problems and tailor Tailscale solutions to align with enterprise buying criteria and procurement processes.
Coordinate with internal stakeholders to translate market feedback into Tailscale product direction and to design and validate sales playbooks that scale across strategic accounts.
Manage multiple concurrent strategic deals and prioritize effectively within a remote work setting to maintain momentum and pipeline health.
Translate pipeline and conversion metrics into accurate forecast data and revenue progress against quarterly and annual targets.
Leverage sales platforms and data tools to manage pipeline, forecast accuracy, and strategic account planning in a remote environment.
Apply general enterprise sales principles to strategic account planning, executive engagement, and long-term relationship building.
Collaborate with engineering, product, and customer-facing teams to ensure solution fit and to address customer needs comprehensively.
Demonstrate consistent activity, honest qualification of deals, and disciplined follow-through to achieve quota and growth objectives.
Requirements
A Bachelor's degree in a relevant field is required for this position.
United States work authorization is required for this role, and sponsorship is not available.
The ability to manage multiple concurrent strategic deals and prioritize effectively in a remote work setting is required.
Candidates must be able to operate independently with strong ownership and accountability for results.
Strong verbal and written communication skills are required to engage executives and influence stakeholders at all levels.
Experience with consultative and strategic enterprise sales methodologies is required.
The capacity to analyze complex business problems and translate them into technology solutions is required.
Proficiency with sales platforms and data tools to manage pipeline and forecasting in a remote setup is required.
Practical notes
This position is based in the United States under a remote work arrangement.
Career growth and typical interview steps are outlined in the Career growth and Typical interview steps sections below.
Typical interview steps
Sales hiring often includes a role play, a discovery call simulation, and a presentation. Candidates may be asked to pitch a product to a panel or handle a tough objection. Behavioral questions focus on past quota attainment and deal history. Energy and preparation matter. Interviewers often simulate the job in the interview itself, so be ready to run a short discovery call or demo. Practicing your own sales pitch out loud helps.
About the company
Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more.