Jason Westerberg

GTM Engineer

Giga

Revenue OperationsBalancedEnterpriseOn-site📍 San Francisco, CA
Deal Size: $100K+ ACV
Sales Cycle: 2-4 months
Posted by Jason Westerberg•

Overview

You're a technical person who lives in the revenue org, not engineering. You maintain and optimize Giga's GTM tech stack (CRM, automation, data pipelines) while also doing customer-facing technical work—scoping implementations, building demos, troubleshooting technical objections. You report to the Head of RevOps (Jason, who posted this) and work with AEs, SEs, and CS on deals and deployments.


Role Snapshot

AspectDetails
Role TypeGTM Engineer (hybrid RevOps + Solutions Engineer)
Sales MotionEmbedded in revenue team across pre-sales and post-sales
Deal ComplexityEnterprise AI support implementations
Sales CycleLikely 2-4 months for enterprise AI deals
Deal SizeLikely $100K+ ACV for enterprise support platform
Quota (est.)No quota - measured on pipeline influence and tech stack optimization

Company Context

Stage: Early-stage (likely Seed/Series A based on 83 employees)

Size: 83 employees

Growth: Actively hiring for new GTM roles (this position is brand new)

Market Position: Competing in crowded AI support/automation space against established players and other AI startups


GTM Reality

Pipeline Sources:

  • Unknown mix of inbound/outbound (company is small enough that every deal matters)
  • Selling AI agents to enterprise support teams requires education and proof of concept
  • Long sales cycles typical for AI infrastructure replacing human workflows

Sales Team Structure: Small team at 83 employees total—likely <10 quota-carrying reps

SE Support: This role IS the technical support for sales—you're it


Competitive Landscape

Main Competitors: Other AI support platforms, traditional support automation tools, building in-house AI solutions

How They Differentiate: Focus on handling complex support workflows at scale with high resolution accuracy

Common Objections: "AI can't handle our complex support scenarios", "We're building this internally", "How do we maintain control/quality?", security/compliance concerns

Win Themes: Demonstrable ROI on support efficiency, proven accuracy metrics, faster than building in-house


What You'll Actually Do

Time Breakdown

Tech Stack Work (40%) | Deal Support (35%) | Customer Implementations (25%)

Key Activities

  • GTM Systems Work: Maintain Salesforce, build automation in tools like Zapier/Make, create reporting dashboards, clean data, troubleshoot integrations. The unglamorous ops work that keeps the revenue engine running.
  • Pre-Sales Technical Support: Jump on calls when prospects have technical questions, build custom demos showing how Giga's AI handles their specific support scenarios, scope implementation complexity and timeline.
  • Customer Implementation Support: Help CS team deploy Giga's AI agents for new customers—configure workflows, integrate with their support systems, troubleshoot issues during rollout.
  • Pipeline Analysis: Pull data on where deals are getting stuck, which technical objections are most common, what integrations prospects need most. Feed this back to product and sales.

The Honest Reality

What's Hard

  • You're defining this role from scratch—there's no playbook. Jason has a vision but you'll need to figure out where you add most value.
  • Context switching constantly: one hour you're in Salesforce building reports, next hour you're on a customer call explaining API capabilities, then back to fixing a broken integration.
  • You're technical but not a full engineer—you might get pulled into customer asks that require actual engineering resources, and you'll be the translator/project manager.
  • In-office 5 days/week in SF is non-negotiable. That's a real constraint.
  • At 83 people, every deal matters and there will be pressure to help close. You'll get pulled into firefighting.

What Success Looks Like

  • Technical win rate improves—fewer deals lost to "too complex to implement" or "security concerns"
  • RevOps tech stack is reliable and AEs/CSMs stop complaining about CRM/tooling issues
  • Customer implementations go smoother because you scoped them properly upfront
  • You become the go-to person for "is this technically possible?" questions across the revenue team

Who You're Selling To

Primary Buyers:

  • VP/Director of Customer Support (budget owner)
  • Head of Support Operations (day-to-day user)
  • CTO/VP Engineering (technical validation, security review)

What They Care About:

  • Proof their complex support scenarios can actually be handled by AI
  • ROI calculation—cost per ticket vs human agents
  • Implementation timeline and risk to existing support operations
  • Security, compliance, data handling (especially for enterprise)
  • Integration with existing support stack (Zendesk, Intercom, Salesforce Service Cloud)

Requirements

  • Strong technical skills—you can write scripts, understand APIs, troubleshoot integrations independently
  • Experience in a GTM/revenue org—you understand how sales and CS teams work, what they need from systems
  • Comfortable customer-facing—you can explain technical concepts to non-technical buyers without being condescending
  • Self-directed—this role doesn't exist yet, you need to figure out priorities and carve out your impact
  • Based in SF and willing to be in office 5 days/week at HQ
  • RevOps or sales engineering background ideal—you've lived in the intersection of technical and revenue work before