From IC To Partnership Director: How Getting “Hands On” With AI Advanced My Career

Expert advice from Gwen Sioson (AI Strategic Partnerships Director, ActiveCampaign) and Justin Zimmerman (Founder, Partnerplaybooks).

Snapshot

You do not need to wait for a director title before you start operating like a director. Instead, turn your individual contributor execution skills into systems that create leverage for teammates, partners, customers, and leaders. Gwen’s path at ActiveCampaign shows what that looks like in practice: build firsthand experience with emerging technology, create useful market intelligence, lead sharper cross-functional conversations, and identify the work the organization will soon need before a formal role exists.

AI makes this transition more accessible, but it also raises the standard. It is no longer enough to bring a concept document into a product meeting and hope someone prioritizes it. You can prototype an idea, pressure-test it, learn the tools, and arrive with something tangible. The risk is staying in task mode while the market shifts around you. The upside is becoming the person who sees the gap, helps others understand it, and builds the path forward.

Keep reading to learn how Justin Zimmerman and Gwen Sioson can help you build credibility, create strategic leverage, and lead cross-functional change.

“Director-level work is about designing systems that help you, your teammates, and the entire organization move forward.” – Gwen Sioson

Table of Contents

• Snapshot
• Build the role before you ask for the title
• Create time to become a builder
• Turn execution skills into strategic leverage
• Build an AI intelligence system for the market
• Replace checkbox meetings with decision meetings
• See the market shift and create the opportunity
• Use a pilot to prove director-level capability
• Take the losses, repair the relationship, and learn
• Use AI as a coach before you go internal
• Build first, then decide whether to buy or scale
• Tools
• FAQs
• Conclusion

Build the role before you ask for the title

Gwen’s story is not about getting promoted because she waited patiently for an opening. It is about recognizing that the market, product, and partner ecosystem were changing, then stepping into the work required by that change.

After nearly seven years at ActiveCampaign, Gwen moved from an individual contributor role into Director of Strategic Partnerships with a focus on AI. The transition was not simply a change in title. It required changing the operating model from completing assigned projects to designing systems that help many people make better decisions and move faster.

That distinction matters. As an IC, you are often rewarded for being reliable, self-directed, and excellent at execution. You receive a project, build the plan, coordinate stakeholders, and drive a result. Those capabilities remain essential as a director, but they are no longer the full job.

At the director level, you need to ask different questions:

• What system will make this work repeatable for the team?
• Which priorities are changing across product, engineering, marketing, and partnerships?
• What does the market shift mean for customers and partners?
• Where is there an unowned value gap that needs leadership?
• How can you create the conditions for better decisions, not merely request them?

That is why a career move like this cannot depend only on ambition. You need evidence. You need cross-functional trust. And you need a body of work that shows you can create clarity when the path is not obvious.

“When you have built something and shown results, you earn credibility to contribute to decisions instead of merely sitting in the room.” – Gwen Sioson

Create time to become a builder

The first pushback is predictable: building takes time. And time is scarce. Gwen is a remote worker and a parent of two, so this is not advice built on imaginary empty calendars. Her point is simple: if you want to develop strategic range, you have to intentionally make room for deep thinking and hands-on learning.

For Gwen, the time once spent commuting became an early-morning block for reading and thinking. It is not about forcing an identical routine onto your own life. It is about finding a protected window that actually works. That might be a quiet morning, an hour on a weekend, or a recurring block when your energy is strongest.

Use that time for work that compounds:

• Read market news and product updates that affect your partners or customers.
• Explore new AI tools from the perspective of a real user.
• Build a small prototype rather than only researching an idea.
• Write down patterns, risks, and opportunities you can bring back to the organization.
• Learn enough to have a substantive conversation with product and engineering.

Gwen demonstrated this mindset by building and launching a passion project over a July Fourth weekend in 48 hours. She used tools such as v0, connected a database, configured a domain, and set up DNS. The goal was not to become an engineer overnight. The goal was to understand what it takes to bring an idea from zero to a live experience.

That firsthand exposure is career capital. It helps you understand the customer journey, the friction in the tools, the choices required to ship, and the language technical teams use to solve problems. It also gives you a much better instinct for what is feasible, what needs more discovery, and where a partner can add value.

Building in public can be more valuable than building in isolation. A small, real project creates feedback and gives you something concrete to discuss. It turns abstract curiosity into usable intelligence.

“It is better to build in public than to build in silos.” – Gwen Sioson

Turn execution skills into strategic leverage

Gwen began her partnerships career in sponsorships with the San Francisco Giants, then moved into partner marketing at Salesforce Essentials. She helped bring the ActiveCampaign partnership to market from end to end. That experience built the foundation for her later leadership role because it required more than coordinating a campaign.

To bring a partnership to market, you must understand channels, adoption, acquisition, positioning, internal processes, and the practical work required to make a strategy real. You cannot hand a plan to someone else and assume execution will happen automatically.

This is the critical translation from IC to director: do not abandon your execution mindset. Expand it. Your ability to roll up your sleeves with marketing, product, and engineering becomes the source of your credibility. You understand the strategy because you understand the work.

When you are working toward a director role, build a reputation for doing three things consistently:

1. Connect strategy to outcomes. Explain how an initiative drives adoption, acquisition, retention, partner value, or customer value.
2. Connect teams to one another. Bring the right people into the conversation early instead of treating alignment as a final approval step.
3. Connect insight to action. Translate a market signal, customer request, or partner opportunity into a practical next move.

This is especially important in partnerships, where the work can easily become a list of requests. A wish list is not a priority list. Until you have alignment, capacity, a clear value case, and shared ownership, it is only an idea.

For a deeper operational view of how partnerships become a strategic growth engine, explore this guide to building partnership programs that scale.

“You do not put a plan together and expect other people to figure it out. You work alongside the people who will make it real.” – Gwen Sioson

Build an AI intelligence system for the market

One of the first systems Gwen developed as she moved into a director role was a way to turn overwhelming streams of daily news into useful, decision-ready intelligence.

Most people subscribe to newsletters, skim a few headlines, and leave the rest unread. That is understandable. The volume is intense, and no one has time to manually synthesize every market update. But market awareness matters more when technology, buyer expectations, and partner ecosystems are moving quickly.

Gwen’s approach is to use an LLM to create a structured intelligence package from trusted newsletters such as TLDR. Rather than receiving a generic summary, create a reusable prompt or agent that produces three layers of analysis:

1. A neutral summary. What happened, stated clearly and without hype.
2. Your company relevance. Why might this matter for your product, customer base, partnerships, or go-to-market strategy?
3. A counterargument. What could make this update less important, harder to act on, or strategically different than it first appears?

The third layer is the differentiator. It protects you from treating every AI announcement as urgent. It forces you to consider adoption barriers, market timing, internal capability, customer fit, and alternative explanations. In other words, it moves you from consuming news to developing judgment.

Once the intelligence is packaged, it becomes useful across the organization. You can take a focused insight to a product leader, marketing partner, engineering teammate, or executive sponsor and initiate a timely discussion about strategy. That is much more valuable than forwarding a headline with no point of view.

The pace of the market means you cannot wait three or four weeks to adjust every plan. Gwen’s lesson is that partnership strategies need to evolve dynamically. A weekly intelligence rhythm can help you spot where to investigate further, what to ignore, and what needs a leadership conversation now.

A simple weekly intelligence prompt structure

• Summarize the update in three neutral bullets.
• Identify the affected customer, partner, or product segment.
• Describe one potential opportunity for your company.
• Describe one risk or reason to deprioritize the signal.
• Recommend a single person or team to consult next.

AI is not replacing strategic thinking here. It is making the raw inputs manageable so you can spend more time on interpretation, relationships, and action.

“Static newsletters become valuable when you translate them into intelligence that helps your teams make decisions.” – Gwen Sioson

Replace checkbox meetings with decision meetings

The second system is about meetings. Many ICs approach meetings with a personal checklist: share an update, get an answer, secure a handoff, move to the next item. That approach works for managing work, but it rarely produces the cross-functional decisions required for strategic change.

Gwen reframed scheduled meetings as spaces for discussion, debate, and prioritization. The expectation is not that every attendee arrives with the same answer. The expectation is that everyone has used available intelligence to form an informed opinion.

When people have a point of view, they can defend it. When they defend it, assumptions surface. Those assumptions often reveal the important details: a customer constraint, an engineering dependency, an overlooked risk, or a stronger way to sequence the work.

Instead of using 30 minutes to walk through status updates, design the meeting around a decision:

• What decision must be made or prepared for?
• What evidence does each team need to bring?
• Which tradeoffs are on the table?
• What is the cost of choosing one option over another?
• Who will package the options for the next decision-maker?

AI note-taking tools can support this process by capturing the discussion, alternatives, open questions, and next steps. The notes are not the strategy. They are the operational record that keeps the decision moving after the meeting ends.

At ActiveCampaign, Gwen described shortening decision cycles from three or four weeks to no more than two weeks by working hand in hand with product and engineering on dynamic prioritization. That kind of speed does not come from adding more meetings. It comes from increasing the quality of the conversations inside them.

For teams working through AI adoption, a disciplined crawl, walk, run approach can prevent chaos. This practical AI playbook for partner teams offers a useful framework for building that foundation.

See the market shift and create the opportunity

One of the most powerful parts of Gwen’s career story is that the director role did not simply appear as an open requisition. She saw a strategic gap created by a changing market and helped shape the work that would fill it.

ActiveCampaign introduced Active Intelligence, an autonomous marketing solution designed to support small and medium-sized businesses with digital marketing needs. Before that public direction was fully visible, Gwen was participating in planning with partners, developers, engineers, and leadership around what it would take to become agent-platform ready.

The work involved thinking beyond traditional API connections and data synchronization. The emerging need was a customer context layer that could connect systems through Model Context Protocol, commonly called MCP. You can explore the underlying open standard through the Model Context Protocol documentation.

Gwen and her collaborators considered which ecosystems were already MCP-ready, what ActiveCampaign would need as an MCP client platform, and how partners could be supported in designing their own MCP servers. The strategic value was not merely technical integration. It was helping partners, customers, and platforms connect context across systems in a new way.

This is what it means to create an opportunity instead of waiting for one:

1. Pay attention to where the market is moving.
2. Understand where your product is moving.
3. Identify the new work created by the intersection of those two forces.
4. Bring the right internal and external people into a shared planning process.
5. Deliver value before the title is formally attached to the work.

Gwen’s director-level contribution was not an isolated idea. It was preparation. She developed a point of view before the category became crowded, created a strategy with partners and technical teams, and helped establish a direction that others could act on.

“You lead by uncovering opportunities for your teammates and partners, not by waiting on the sidelines for instructions.” – Gwen Sioson

Use a pilot to prove director-level capability

At some point, a role change needs proof. Gwen had an opportunity to take on expanded strategic work during a four-month pilot while teammates took parental leave. Not every organization will present that exact circumstance, but the principle applies broadly: find a bounded opportunity to demonstrate the next level of responsibility.

A useful pilot has a clear scope, a defined time period, cross-functional stakeholders, and measurable outcomes. It should give you room to operate beyond your current role while preserving enough structure that leadership can evaluate what happened.

Do not treat a pilot as a chance to issue orders from a new position of authority. Gwen’s approach was collaborative. She worked with people, contributed directly, and used data to show what the expanded strategy could accomplish.

When you want to make a case for a larger role, build your business case around evidence:

• The business gap or market opportunity you are addressing.
• The work that is currently unowned, underserved, or fragmented.
• The partners and internal teams affected by the gap.
• The strategy and operating system you propose.
• The signals that will show the pilot is creating value.
• The leadership scope required to sustain the work.

The strongest promotion conversation is not, “I have been doing a lot, so I deserve a bigger title.” It is, “This is the business need, this is the work I have already led, this is the evidence, and this is why the organization needs a durable role to continue it.”

Take the losses, repair the relationship, and learn

There is no honest leadership story without mistakes. Gwen’s most important lesson from her pilot was about prioritization. You can build a strategy that looks excellent on paper and still fail if you have not taken the time to understand the priorities, constraints, and workload of the people expected to execute it.

This is a classic internal partnership challenge. Your initiative might be important, but it is not automatically the most important thing for another team. If you do not understand their roadmap, commitments, staffing, customer obligations, and competing goals, your request may become friction instead of momentum.

Gwen’s adjustment was direct: begin conversations by asking where the other person’s priorities are today and how you can support their primary work. That creates space to identify a shared path rather than demanding placement at the top of someone else’s list.

She also did something that takes real humility. After making incorrect assumptions, she created individual apology messages and videos for teammates. The objective was not to defend the original plan. It was to acknowledge the miss, demonstrate learning, and reopen the conversation around how to bring the priority to life together.

This is a powerful standard for leadership. Repair is part of the job. When your assumptions create harm or strain, own your contribution quickly and specifically.

Use this prioritization conversation before requesting work

1. What are the top priorities your team is accountable for right now?
2. What commitments, dependencies, or capacity constraints should I understand?
3. Where does this proposed initiative overlap with your existing goals?
4. What evidence would make this worth prioritizing?
5. How can I reduce effort or remove an obstacle for your team?

Empathy is not separate from execution. It is how cross-functional execution becomes possible.

“Your priority will not become someone else’s priority until you understand their work, build the relationship, and make the value clear.” – Gwen Sioson

Use AI as a coach before you go internal

Justin added an important layer to the conversation: the transition from IC to director is often difficult because you may not have a coach guiding every decision. You are learning how to lead through people, not merely through your own output.

AI can be useful as a calibration tool before you bring an idea to internal stakeholders. You can lay out the circumstances, explain the desired outcome, identify the people involved, and ask for alternative ways to frame the conversation. The goal is not to outsource judgment or let an LLM decide how to manage relationships. The goal is to challenge your first instinct and prepare more thoughtfully.

Before a sensitive meeting, use AI to explore:

• What assumptions might I be making about this team?
• What objections or constraints should I anticipate?
• How can I express the business value without minimizing their workload?
• What questions would help me understand the situation better?
• How can I present several options instead of one fixed request?

The key reminder is that a director role is a service role. You are not there to impose authority. You are there to help people and teams accomplish better work in a coordinated way.

Build first, then decide whether to buy or scale

When asked about the buy versus build question for AI agents, Gwen’s perspective was clear: if you want to commercialize or prioritize an agent idea, first put yourself in the customer’s shoes. Try building a version of it yourself and prove the concept.

This does not mean every organization should build every tool internally. It means you should develop enough firsthand experience to evaluate the opportunity intelligently. Building a prototype or minimum viable product teaches you where the real complexity lives. You discover tools, techniques, customer questions, failure points, and possible outputs that would remain invisible in a slide deck.

That knowledge changes the conversation with product and engineering. Instead of presenting a vague request, you can show the concept, explain the use case, identify what you learned, and collaborate on what a stronger version could become.

You do not need an engineering degree to do this. Natural-language interfaces and AI-enabled building tools have reduced the distance between a business idea and a usable prototype. Your leverage comes from being able to show and tell.

The old model was bringing a document and hoping it got scoped. The new opportunity is bringing a prototype, discussing a version two with product and engineering, and shortening the path from ideation to marketability.

Tools

The right tool stack should support your thinking, not replace it. The following tools and categories reflect the working methods discussed by Gwen and Justin.

• LLM of choice: Use a large language model to synthesize market news, pressure-test a strategy, generate counterarguments, and prepare for difficult conversations.
• TLDR: Use a relevant newsletter source as an input for an AI-powered intelligence workflow.
• AI note taker: Capture decisions, options, owners, and unresolved questions after cross-functional discussions.
• v0: Build prototypes quickly with natural-language workflows and gain firsthand product-building experience.
• Database and domain tools: Connect the practical pieces of an idea, including data storage, domains, and DNS, so you understand the journey from concept to live product.
• MCP resources: Build familiarity with Model Context Protocol concepts as agentic systems and partner ecosystems evolve.

Start with one workflow that solves a real problem. A weekly intelligence brief, a meeting-preparation prompt, or a simple customer-facing prototype is enough to begin. The goal is repeatable learning, not a perfect tool stack.

FAQs

How do you move from an IC role to a director role?

You move by expanding from individual execution into organizational leverage. Build systems that improve how teams gather intelligence, make decisions, prioritize work, and collaborate. Then document the business value of the broader work you are already leading.

Should you wait for a director position to open?

No. Look for a business gap created by a market shift, product change, customer need, or partner opportunity. Lead the work needed to address that gap, build cross-functional support, and use a pilot or measurable initiative to prove the role is needed.

How can AI help partnership leaders?

AI can help you turn market news into structured intelligence, prepare for conversations, create prototypes, document meetings, and explore alternatives before making a recommendation. It should increase your capacity for strategic thinking and relationship building, not replace either one.

What is the biggest mistake when leading cross-functional work?

Assuming that a strong strategy automatically becomes someone else’s priority. Start by understanding each team’s commitments, constraints, and goals. Build a shared value case and show how the work can fit into the broader roadmap.

Do you need technical training to build AI agents or prototypes?

You do not need to be an engineer to start building. Natural-language AI tools can help you prototype ideas and understand the customer experience. The purpose is to gain enough firsthand knowledge to collaborate more effectively with product and engineering teams.

Conclusion

Your path from IC to director is not a mystery title change. It is a shift in how you create value. Build the habit of learning the market, getting your hands on the tools, translating insight into action, and working with real empathy for the people who must help execute the strategy. Gwen’s example is a reminder that opportunities often seek the people who are prepared enough to recognize them. Build the prototype. Create the system. Repair the miss when you make one. Then make the business case for the leadership role the work already demands.