Senior Director - Salesforce + AI

Who We Are

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’re a team of 25, driven by results, with plans to scale. 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 Senior Director sets the standard — for client ownership, team leadership, and firm direction. You're running a large, complex portfolio at the executive level while simultaneously shaping how Skydog grows. Clients at this level don't just hire you to deliver; they call you before they make major decisions. Internally, you're setting the bar for client delivery.

What You're Actually Doing
Owning a multi-million dollar book of business. You're the ultimate executive relationship owner across a large portfolio of clients. C-suite trust, renewal strategy, and expansion are in your camp. Any client, any size, any complexity.
Shaping firm direction. You're not just executing on a playbook; you're writing it. You see gaps in how Skydog prices, packages, and positions its services, and you close them. Your experience directly influences our offerings, processes, and company vision.
Developing and holding the team accountable. You're the standard everyone else is measured against. You give direct feedback, build careers, and don't let underperformance linger. Your job isn't just to run your clients; it's to make everyone around you better.
Anticipating what's coming. You're reading the market before clients are. AI is reshaping every business process. You're advising on what's next and positioning Skydog to lead, not react.
Serving as a trusted advisor at the executive level. You handle sensitive, high-stakes conversations (escalations, strategic pivots, etc.) with composure and influence. You are constantly looking to deepen client relationships.
Ensuring best-in-class technical delivery. You're building and overseeing complex, high-impact client solutions with long-term results. You set the architectural standard, champion innovation in tooling and methodology, and make sure solutions deliver the intended value.

What We're Looking For
You've run large, complex accounts. $1M+ book. C-suite relationships. Clients that relied on you as a strategic advisor, not just a vendor.
You've built and developed teams. You have directly managed 2+ people in a fast-paced environment. You've coached and held people to a high standard. Teams perform better because of you.
Your business IQ is exceptional. You think like an operator. You translate client problems into architecture decisions, and market shifts into strategic recommendations. Executives trust your read on situations.
You have real executive presence. You've navigated difficult, high-stakes conversations at the senior level and come out with the relationship stronger. You align both clients and internal teams around a vision.
You have a strong technical foundation. You know what "excellent" looks like across Salesforce, HubSpot, and AI-native workflows.
You want to win and help Skydog win. This isn't a role for someone who wants to manage a book. It's for someone who wants to grow it, raise the bar, and leave Skydog better than they found it.
Why it's awesome to work at Skydog
A role with true autonomy and ownership — no red tape
Access to high-impact projects where your work is seen and appreciated
Opportunity to earn equity
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: $210,000 - $225,000