Director - Salesforce + AI

About Skydog

Skydog Ops builds CRM and AI systems that actually work: Salesforce and HubSpot implementations that go live on time, and AI-native workflows that automate the work your team is currently doing manually. We are one of the fastest-growing AI transformation and RevOps implementation firms in the US and the highest-rated Salesforce + HubSpot implementation firm on G2.

Our clients include large scale financial services firms (asset managers & banks) and high-growth B2B tech companies. We have ~20 people with plans to scale. We have a team driven by results. The best people we hire lean into their work, own the outcomes, and experience a ton of career growth from expanded leadership opportunities.

Role Overview

A Skydog Solution Architect runs engagements. Not from a distance, but hands-on. You're carrying 2–5 active client relationships at a time on engagements ranging from quick implementations to multi-year, strategic relationships. You are technical enough to design + build complex processes and have the leadership skills to present and defend your work to a skeptical CTO.

What you'll do

• Owning your book of clients. 2–5 engagements at any given time. You're running kickoffs, driving architecture decisions, managing scope, and having difficult conversations when things aren't working. Client satisfaction, measured by retention, is your primary metric.
• Building and configuring, not just advising. You're hands-on in Salesforce (Sales Cloud, Service Cloud, FSC, Revenue Cloud, Marketing Cloud, Agentforce) and HubSpot. Complex Flow automation, data model design, and integration architecture. You're not delegating the hard technical work, you're doing it or directly overseeing it.
• Designing AI-native workflows. You're not just configuring Salesforce - you're building systems where AI does real work. That might mean automating research and enrichment pipelines, building AI agents that act on CRM data, or integrating LLMs into client-facing processes. You don't need to be an ML engineer, but you need to have built something that works.
• Driving outcomes, not status updates. Clients don't pay us to build cool things. They pay us to move their business forward. You know the difference between a project that's “on-schedule” vs one that's driving value.
• Leading a small delivery team. You're not just running your clients; you're leading the consultants and admins working alongside you. That means real feedback, setting standards, and not letting underperformance linger. Prior people management experience is a plus but less important than your instinct for it.

What we're looking for

• You've delivered complex CRM or AI implementations. Not as a supporting player. You've architected solutions on Sales Cloud, FSC, or Revenue Cloud at companies with real complexity: multiple business units, non-trivial data models, integrations to external systems.
• You are a leader. You've managed scope, navigated difficult clients, and shipped things that held up after go-live.
• You have great business judgment. From designing complex architecture to talking shop with executives, your business IQ defines how you operate.
• You move fast and it shows. Most of the build out is done by the first demo. Clients know they get speed and accuracy with you + your team.
• You want to win. This role is for somebody looking to crush it. Your bar is excellence. You own your wins and losses - you’re proud of the wins and learn from losses.

Benefits

• A role with true autonomy and ownership—no red tape
• Access to high-impact projects where your work is seen and appreciated
• Tight-knit team with shared values and high standards
• Meaningful earnings and growth potential
• 2 annual team offsites
• Great benefits: health insurance, 401k, flexible PTO, and more
• Salary Range: $170,000-180,000