# Director, Strategic Sales

**Company:** [Tailscale](https://hotfix.jobs/companies/tailscale)
**Location:** Remote
**Role:** Account Executive
**Salary:** $350k – $400k/yr
**Experience:** 8+ years
**Skills:** SaaS, Enterprise Sales, strategic sales, Outbound Prospecting, Account Planning, Sales Forecasting, Pipeline Management, executive engagement, Negotiation, Go-to-Market Strategy, gtm engineering, Customer Success, sales coaching, territory strategy, deal qualification
**Posted:** 2026-08-04

> Leads the creation of a strategic enterprise sales organization, personally closes complex opportunities, and builds a team serving organizations with more than 10,000 employees. The role requires 5+ years as a top technology sales representative and a record of winning large SaaS deals.

## Job Description

## Responsibilities

### Build a New Business
- Build Tailscale's Strategic Sales organization from the ground up.
- Design the operating model, territory strategy, account segmentation, and engagement approach.
- Develop repeatable playbooks for winning large enterprises.
- Shape the long-term vision for Strategic Sales as the business scales.
- Partner with executive leadership to influence go-to-market strategy for major customers.

### Lead From the Front
- Own a portfolio of high-value strategic accounts.
- Lead complex, multi-stakeholder sales cycles from initial engagement through expansion.
- Develop executive relationships with CIOs, CISOs, CTOs, Chief Architects, infrastructure leaders, and other senior decision-makers.
- Serve as the executive quarterback on major strategic pursuits.
- Negotiate complex commercial agreements across technical, financial, legal, and executive stakeholders.

### Build an Elite Team
- Recruit, hire, and develop Strategic Account Executives.
- Initially lead approximately 3–5 Strategic Account Executives.
- Coach account strategy, executive engagement, negotiation, forecasting, and deal execution.
- Foster a high-performance culture built on accountability, collaboration, curiosity, and continuous learning.

### Create Pipeline
- Lead an outbound-first sales motion.
- Prospect into strategic accounts and build executive relationships.
- Partner with SDRs, Marketing, GTM Engineering, Customer Engineering, and Customer Success on account plans.
- Create scalable account-planning and outbound strategies that generate qualified pipeline.
- Establish best practices for strategic prospecting, account planning, and executive alignment.

### Drive Operational Excellence
- Own account planning, forecasting, pipeline health, and business planning for the Strategic segment.
- Inspect deal strategy and qualification throughout the sales cycle.
- Use data to improve execution, identify trends, and optimize performance.
- Partner with Product and Engineering to provide market feedback that influences product direction.
- Build the operating rhythm, metrics, and inspection processes needed to scale.

## Requirements
- 5+ years as the top sales representative at a high-growth technology company.
- Proven success selling to organizations with more than 10,000 employees.
- Demonstrated ability to close complex six-, seven-, and eight-figure SaaS opportunities.
- Consistent record of building outbound pipeline and winning net-new enterprise customers.
- Executive presence and ability to engage CIOs, CISOs, CTOs, and senior business executives as a trusted advisor.
- Strong business acumen and experience navigating complex buying committees and long enterprise sales cycles.
- Comfort operating in ambiguity and building new processes.
- Passion for building teams, developing people, and creating scalable organizations.

## Compensation & Benefits
- Target OTE: **$350,000–$400,000 USD**.
- Compensation includes base salary, equity, and comprehensive benefits.
- Flexible, inclusive work environment.
- Equity incentive plan.

## Similar roles

- [Strategic Account Director, Federal](https://hotfix.jobs/jobs/8f2d66e1-259e-4801-8dca-8c3bf5dde332) - Decagon - Remote - $350k – $400k/yr
- [Majors Account Director - Key Customers](https://hotfix.jobs/jobs/209c3f64-df40-4d41-adc3-4893260dcd68) - Grafana Labs - Remote - $350k – $380k/yr
- [Director of Mid-Market Sales](https://hotfix.jobs/jobs/cbbcdf30-f110-49d7-99a4-1c53eb39cf7a) - Vapi - San Francisco, CA - $350k – $400k/yr
- [Director, Sales](https://hotfix.jobs/jobs/df39f387-bb95-4497-83c5-61e64877afe8) - Ironclad - Remote - $350k – $400k/yr
- [Regional Sales Director](https://hotfix.jobs/jobs/fe9140c5-8871-44b9-ac5c-14bfb6d5ccf6) - Sourcegraph - Remote - $360k – $360k/yr

**Apply:** https://hotfix.jobs/jobs/e7198a70-671b-4c5b-a8c1-0375d0182cd0
**Canonical:** https://hotfix.jobs/jobs/e7198a70-671b-4c5b-a8c1-0375d0182cd0