Sr. Director/Head of Sales - Gia

G-P

16d•$136,000 - $170,000

About The Position

GIA is an AI SaaS product with a product-led sales GTM: the product generates adoption and intent; Sales accelerates conversion, expands accounts, and closes larger/compliance-driven deals. You will build and lead a high-performing sales function that converts PQLs → pipeline → revenue, partners tightly with Growth/Lifecycle, Product, CS, and RevOps, and creates a scalable, metrics-driven sales engine.

Requirements

10+ years in B2B SaaS sales; 3+ years in sales leadership (Director/Sr Director/Head of Sales)
Proven experience building and scaling a sales org from early stage (0→1 / 1→N)
Demonstrated success in product-led sales or hybrid PLG + enterprise motions
Comfortable selling into regulated or trust-heavy environments (security, legal, compliance, HR, finance)
Strong forecasting and operational rigor; ability to build repeatable process without bureaucracy
Excellent cross-functional collaboration with Product, Growth, CS, and RevOps

Nice To Haves

Experience selling AI/agentic SaaS, workflow automation, or HR/legal tech
Enterprise procurement + security review expertise (SOC2, data privacy, vendor risk)
Background in usage-based expansion / land-and-expand strategies
International selling experience (helpful for global HR/compliance products)

Responsibilities

Revenue leadership (new + expansion)
Own bookings/ARR targets for GIA across new business, upsell, and expansion
Build the GTM plan: segments, territories, coverage model, and channel strategy (as relevant)
Drive consistent forecasting, pipeline hygiene, and operating cadence (weekly/monthly/QBR)
PLS execution: PQL-to-close engine
Define the PQL → SQL → Close workflow with Growth, Product, and RevOps (routing, SLAs, scoring, follow-up playbooks)
Build repeatable sales motions for:
Sales-assist (fast cycles from strong intent)
Mid-market/Enterprise (security, procurement, legal/compliance reviews)
Improve conversion rates at each stage and shorten time-to-close
Upsell to existing customers (if applicable)
Create a structured motion to land GIA into existing accounts: target personas, entry points, champion-building, ROI cases
Partner with CSM/Account teams on joint plans, incentives, and expansion plays
Build a pipeline generation strategy inside the install base (usage + stakeholder mapping)
Team building & coaching
Hire, onboard, and lead the initial team (typically: 1–3 AEs, 1–2 SEs, later SDR/BDR, sales ops support)
Coach for high standards: discovery, value-based selling, security/compliance navigation, multi-threading, MEDDICC (or similar)
Build sales enablement: pitch, demo narrative, competitive positioning, mutual action plans, ROI calculators
Cross-functional leadership
Partner with Product to translate customer feedback into roadmap priorities and packaging decisions
Partner with Growth/Lifecycle to align acquisition, onboarding, and lifecycle nudges to revenue outcomes
Partner with Legal/Security/Finance on repeatable deal desk processes and standard terms