Project Manager / Client Success Lead — Microsoft Partner (Part-Time → Full-Time)
Budget: $50 – $0 USD
Summary
About Us
Wired CIO is a Chicago-based managed IT services provider and Microsoft partner. We help SMBs across the U.S. with managed IT, co-managed IT, Microsoft 365, Dynamics 365 (Business Central + Sales), Power BI / Fabric, AI / Copilot, cybersecurity, and compliance.
We run lean, move fast, and operate everything internally out of a tightly integrated stack — Notion as our single source of truth, n8n for automation, and Claude woven through both. You don't need to already know our stack. We're looking for someone who is genuinely great at running projects and managing client relationships — we'll teach you the tooling.
==
The Role
You will own everything that happens after a client signs — from kickoff through the entire client lifecycle.
You'll work directly with our CEO, CTO, me (CRO), and our Dynamics consultants. Practically speaking, your job is to hold all of us, including me, accountable to what we promised the client — on scope, on timeline, on communication.
You'll be client-facing. You'll run the kickoff. You'll be the single point of contact the client trusts. You'll keep our consultants' work visible, organized, and on track, and you'll keep our clients informed without us having to chase you.
This is fundamentally a soft-skills role. We can teach you Notion. We'll build the n8n backend with you. We can't teach the judgment to spot a client quietly drifting toward unhappy, or the spine to push back on your own internal team when a commitment is at risk.
==
What You'll Do
- Run client kickoffs and translate signed SOWs into structured project plans
- Own the project status, risks, decisions log, and action items for every active engagement
- Be the day-to-day client point of contact — agendas, status updates, meeting notes, follow-ups
- Coordinate consultants (Dynamics, M365, Power BI, AI, cybersecurity) so nothing slips between hand-offs
- Identify when scope, timeline, or expectations are drifting — and surface it early, in writing, with a recommendation
- Help us evolve the post-sales playbook itself: templates, checklists, automations, reporting
==
Required Experience
- 3+ years managing client-facing projects in a professional services, agency, MSP, or consulting environment
- Hands-on experience with any modern collaboration / project management platform (Notion, Asana, ClickUp, Monday, Linear, Smartsheet, etc.)
- Excellent written communication — you can write a status update a CEO will actually read
- Comfort being the adult in the room — pushing back on internal teams, holding clients to their commitments, and saying "no" or "not yet" when needed
- Process-oriented and self-directed — you'll be building parts of this role from scratch, not stepping into a defined PMO
- Genuinely tech-savvy and a quick learner — comfortable picking up new tools, debugging your own workflow, and adapting fast
- U.S. business hours availability (Central or Eastern preferred)
==
Bonus Points
- Background working with SMB clients — owners, operators, in-house IT leads
- Experience using Claude (or another LLM) as part of your day-to-day project workflow — drafting, summarizing, extracting, generating
- Working familiarity with n8n (or comparable tools — Make, Zapier, Power Automate at depth)
==
Double Bonus Points
- Familiarity with Sandler or any consultative sales methodology (helps you understand how we sold the work)
- Microsoft 365 ecosystem fluency (M365, Teams, SharePoint, Dynamics 365)
==
Current Work You'd Be Involved In Right Away
These are three engagements that just closed and are kicking off now — representative of the variety of work you'd be coordinating from day one:
FDA-regulated medical device manufacturer (~10 employees)
A multi-phase, ~6-8 month Dynamics 365 + IT modernization engagement. Phase 1 is a Business Central rollout (financials, AR/AP, serialized inventory for Class II medical devices, ShipStation + e-commerce integrations). Phase 2 layers on an FDA-compliant QMS (CAPA, electronic signatures, document control, SOPs, training, contract manufacturer document management, Computer System Validation). Phase 3 is a full Microsoft 365 Business Premium modernization (Entra ID, Intune, Defender, Autopilot, Teams Phone, SharePoint, HIPAA BAA). Multiple consultants involved across the three phases — this is the engagement that most needs structured coordination.
Multi-paper newspaper publisher (~25 employees)
Co-managed IT engagement supporting a single internal IT lead. Scope includes backup and disaster recovery, file server cleanup, a QuickBooks Enterprise migration onto the new server, firewall management, mixed Mac/PC fleet management, and ongoing co-managed support. Daily publication deadlines drive a low downtime tolerance and high communication standard.
Distribution and field service operation
Integrated Dynamics 365 implementation spanning three modules in one engagement — Dynamics 365 Sales, Field Service, and Business Central — replacing fragmented operational and accounting systems with a single governed platform. This is a high-coordination engagement: multi-module D365 work involves several consultants, parallel workstreams, and a client team that needs a steady single point of contact through go-live.
In addition to these three, you'd also be inheriting and running point on a number of existing managed IT and co-managed clients we already support.
==
Engagement
- Starts part-time — roughly 15-20 hours/week
- Transitions to full-time within 2-4 months for the right person, as our active project load grows
- 100% remote
- Long-term relationship — we're hiring for the next several years, not the next sprint
- Reports directly to me (CRO)
==
How to Apply
Please include in your proposal:
1. A short paragraph on the most complex client project you've personally owned end-to-end — what it was, who was involved, and what you'd do differently if you ran it again
2. A specific example of a client project where you had to hold your own internal team accountable to a client commitment — what happened, what you did
3. Any direct experience with Claude, ChatGPT, n8n, or similar tools inside your project workflows
4. Your hourly rate and weekly availability
Skip the generic Upwork cover letter. We read every proposal, and we can tell.
Thanks for reading — looking forward to talking.
About Us
Wired CIO is a Chicago-based managed IT services provider and Microsoft partner. We help SMBs across the U.S. with managed IT, co-managed IT, Microsoft 365, Dynamics 365 (Business Central + Sales), Power BI / Fabric, AI / Copilot, cybersecurity, and compliance.
We run lean, move fast, and operate everything internally out of a tightly integrated stack — Notion as our single source of truth, n8n for automation, and Claude woven through both. You don't need to already know our stack. We're looking for someone who is genuinely great at running projects and managing client relationships — we'll teach you the tooling.
==
The Role
You will own everything that happens after a client signs — from kickoff through the entire client lifecycle.
You'll work directly with our CEO, CTO, me (CRO), and our Dynamics consultants. Practically speaking, your job is to hold all of us, including me, accountable to what we promised the client — on scope, on timeline, on communication.
You'll be client-facing. You'll run the kickoff. You'll be the single point of contact the client trusts. You'll keep our consultants' work visible, organized, and on track, and you'll keep our clients informed without us having to chase you.
This is fundamentally a soft-skills role. We can teach you Notion. We'll build the n8n backend with you. We can't teach the judgment to spot a client quietly drifting toward unhappy, or the spine to push back on your own internal team when a commitment is at risk.
==
What You'll Do
- Run client kickoffs and translate signed SOWs into structured project plans
- Own the project status, risks, decisions log, and action items for every active engagement
- Be the day-to-day client point of contact — agendas, status updates, meeting notes, follow-ups
- Coordinate consultants (Dynamics, M365, Power BI, AI, cybersecurity) so nothing slips between hand-offs
- Identify when scope, timeline, or expectations are drifting — and surface it early, in writing, with a recommendation
- Help us evolve the post-sales playbook itself: templates, checklists, automations, reporting
==
Required Experience
- 3+ years managing client-facing projects in a professional services, agency, MSP, or consulting environment
- Hands-on experience with any modern collaboration / project management platform (Notion, Asana, ClickUp, Monday, Linear, Smartsheet, etc.)
- Excellent written communication — you can write a status update a CEO will actually read
- Comfort being the adult in the room — pushing back on internal teams, holding clients to their commitments, and saying "no" or "not yet" when needed
- Process-oriented and self-directed — you'll be building parts of this role from scratch, not stepping into a defined PMO
- Genuinely tech-savvy and a quick learner — comfortable picking up new tools, debugging your own workflow, and adapting fast
- U.S. business hours availability (Central or Eastern preferred)
==
Bonus Points
- Background working with SMB clients — owners, operators, in-house IT leads
- Experience using Claude (or another LLM) as part of your day-to-day project workflow — drafting, summarizing, extracting, generating
- Working familiarity with n8n (or comparable tools — Make, Zapier, Power Automate at depth)
==
Double Bonus Points
- Familiarity with Sandler or any consultative sales methodology (helps you understand how we sold the work)
- Microsoft 365 ecosystem fluency (M365, Teams, SharePoint, Dynamics 365)
==
Current Work You'd Be Involved In Right Away
These are three engagements that just closed and are kicking off now — representative of the variety of work you'd be coordinating from day one:
FDA-regulated medical device manufacturer (~10 employees)
A multi-phase, ~6-8 month Dynamics 365 + IT modernization engagement. Phase 1 is a Business Central rollout (financials, AR/AP, serialized inventory for Class II medical devices, ShipStation + e-commerce integrations). Phase 2 layers on an FDA-compliant QMS (CAPA, electronic signatures, document control, SOPs, training, contract manufacturer document management, Computer System Validation). Phase 3 is a full Microsoft 365 Business Premium modernization (Entra ID, Intune, Defender, Autopilot, Teams Phone, SharePoint, HIPAA BAA). Multiple consultants involved across the three phases — this is the engagement that most needs structured coordination.
Multi-paper newspaper publisher (~25 employees)
Co-managed IT engagement supporting a single internal IT lead. Scope includes backup and disaster recovery, file server cleanup, a QuickBooks Enterprise migration onto the new server, firewall management, mixed Mac/PC fleet management, and ongoing co-managed support. Daily publication deadlines drive a low downtime tolerance and high communication standard.
Distribution and field service operation
Integrated Dynamics 365 implementation spanning three modules in one engagement — Dynamics 365 Sales, Field Service, and Business Central — replacing fragmented operational and accounting systems with a single governed platform. This is a high-coordination engagement: multi-module D365 work involves several consultants, parallel workstreams, and a client team that needs a steady single point of contact through go-live.
In addition to these three, you'd also be inheriting and running point on a number of existing managed IT and co-managed clients we already support.
==
Engagement
- Starts part-time — roughly 15-20 hours/week
- Transitions to full-time within 2-4 months for the right person, as our active project load grows
- 100% remote
- Long-term relationship — we're hiring for the next several years, not the next sprint
- Reports directly to me (CRO)
==
How to Apply
Please include in your proposal:
1. A short paragraph on the most complex client project you've personally owned end-to-end — what it was, who was involved, and what you'd do differently if you ran it again
2. A specific example of a client project where you had to hold your own internal team accountable to a client commitment — what happened, what you did
3. Any direct experience with Claude, ChatGPT, n8n, or similar tools inside your project workflows
4. Your hourly rate and weekly availability
Skip the generic Upwork cover letter. We read every proposal, and we can tell.
Thanks for reading — looking forward to talking.