Crestwood Associates

Crestwood Associates Crestwood Associates is an award-winning Acumatica and Microsoft certified partner. We stand by the “Crestwood Trust Guarantee” with our clients: True Experts.

For more than 24 years, Crestwood has been providing innovative technology solutions to accelerate operational efficiencies for mid-market organizations. Best known for delivering unparalleled value to our clients, Crestwood is headquartered in Chicago, serves thousands of clients nationwide, and is rapidly expanding reach across the United States. Software that Works. No Hidden Fees.

If you’re trying to figure out how to scale operations right now, here’s the part most teams miss:Look at how much extra...
03/30/2026

If you’re trying to figure out how to scale operations right now, here’s the part most teams miss:

Look at how much extra effort it takes to keep things working.

If growth is starting to mean:
– more checking before decisions
– more coordination across teams
– more time validating instead of moving

that’s where the conversation starts.

You may be asking yourself:
Can we keep running it like this?
Or is this going to get harder every time things pick up?

That’s the part most leaders sit with longer than they expect.

We broke down where this shows up first and how teams decide if they can keep running it this way.

Getting ready for  ? Our annual Acumatica Event Guide is live and packed with everything you need to prepare, from what ...
01/21/2026

Getting ready for ? Our annual Acumatica Event Guide is live and packed with everything you need to prepare, from what to pack and where to stay to how to navigate Seattle and the Summit app.

Read the guide and get ready for a smooth, seamless Summit experience:

Getting ready for ? Our annual Acumatica Event Guide is live and packed with everything you need to prepare, from what to pack and where to stay to how to navigate Seattle and the Summit app. Read the guide and get ready for a smooth, seamless Summit experience:  

The wait is over. Acumatica’s 2026 MVPs have been announced. 🙌Meet the 101 community leaders who went above and beyond t...
01/21/2026

The wait is over. Acumatica’s 2026 MVPs have been announced. 🙌

Meet the 101 community leaders who went above and beyond this year to share expertise, mentor others, and strengthen the Acumatica ecosystem. Check out our latest blog: http://my.sociabble.com/mfMRop4R36VK

The wait is over. Acumatica’s 2026 MVPs have been announced. 🙌 Meet the 101 community leaders who went above and beyond this year to share expertise, mentor others, and strengthen the Acumatica ecosystem. Check out our latest blog:

01/21/2026

What makes more than just a conference? On the latest episode of The Acumatica ERP Podcast, Sanket Akerkar and Michael Shockley share a sneak peek into this year's Summit, from the new Seattle location to expanded learning and a growing global community.

Listen now: http://my.sociabble.com/XPxc1Y2HLxZ5

As   continues to grow, so does the opportunity to learn and connect. In this Acumatica Podcast episode, Sanket Akerkar ...
01/21/2026

As continues to grow, so does the opportunity to learn and connect. In this Acumatica Podcast episode, Sanket Akerkar and Michael Shockley preview Summit 2026, highlighting the new location, expanded sessions, and the community behind it all.

Listen now and plan your Summit experience:

As continues to grow, so does the opportunity to learn and connect. In this Acumatica Podcast episode, Sanket Akerkar and Michael Shockley preview Summit 2026, highlighting the new location, expanded sessions, and the community behind it all. Listen now and plan your Summit experien...

For many manufacturing and distribution teams, year-end inventory reviews raise a bigger question than expected: Are the...
01/12/2026

For many manufacturing and distribution teams, year-end inventory reviews raise a bigger question than expected: Are these discrepancies operational issues, or system limitations surfacing under pressure?

This article explains how post year-end inventory results often expose reporting gaps, process constraints, or visibility issues that legacy systems struggle to handle and how leaders can interpret the signals correctly before making their next move. Read More Below:

Practical guidance for manufacturing and distribution teams on reviewing year-end inventory variances without overreacting or disrupting operations.

1099 compliance just got harder.New forms. New thresholds. More risk.That’s why Crestwood and Avalara are teaming up on ...
11/13/2025

1099 compliance just got harder.
New forms. New thresholds. More risk.

That’s why Crestwood and Avalara are teaming up on November 18th at 12:00p CT to break it all down and show you how to:
✔️ Manage W-9 and W-8 contractors without the headaches
✔️ File new 1099s like NEC, DA, and K with confidence
✔️ Automate reporting and stay audit-ready

Keep compliance from becoming chaos.
Register Now: https://hubs.li/Q03M632R0

IRS rules keep changing... are your 1099 and W-9 processes keeping up?On November 18th at 12:00p CT, Crestwood and Avala...
11/05/2025

IRS rules keep changing... are your 1099 and W-9 processes keeping up?

On November 18th at 12:00p CT, Crestwood and Avalara will walk through the latest compliance updates and how to:
✔️ Simplify contractor management (W-9/W-8)
✔️ Stay ahead of new 1099 forms (NEC, DA, K)
✔️ Reduce risk with automated reporting

Get the tools you need to stay compliant and stress-free.
Register Now: https://hubs.li/Q03M62sl0

Staying compliant with 1099 and W-9 requirements is getting more complex. Between new filing thresholds, a brand-new 109...
10/28/2025

Staying compliant with 1099 and W-9 requirements is getting more complex. Between new filing thresholds, a brand-new 1099 form, and the need to collect W-8s for overseas contractors, the rules are shifting fast.

Join Crestwood and Avalara on November 18th at 12:00p CT for a webinar that covers how to:
✔️ Navigate common 1099 compliance challenges
✔️ Manage contractors with W-9 or W-8 tax status
✔️ Report more accurately, including NEC/MISC, 1099-DA, and 1099-K
✔️ Leverage Avalara for full-cycle management

Don’t miss practical strategies to simplify compliance and reduce risk.
Register Now: https://hubs.li/Q03M5_hD0

For more than 25 years, Crestwood Associates has partnered with Microsoft Dynamics GP clients who rely on their systems ...
10/27/2025

For more than 25 years, Crestwood Associates has partnered with Microsoft Dynamics GP clients who rely on their systems daily and we understand the frustration of slowing updates, complex integrations, and rising maintenance costs.

That’s why our CMO & Business Integrator, Stephanie McColly, is hosting a free one-hour session on November 5 at 1 PM ET to help GP users understand what’s changing, what’s next, and how to prepare on their own timeline.

Join Crestwood Associates, Avalara, and ADP for a practical conversation designed to help you plan confidently for the future of your ERP.
Register here: https://hubs.li/Q03QhwHF0

Thinking about moving from GP to Acumatica? You’re not just changing systems you’re changing how your business operates....
10/08/2025

Thinking about moving from GP to Acumatica? You’re not just changing systems you’re changing how your business operates.
Link:https://hubs.li/Q03LJVwx0

Join us on November 5 for a practical workshop hosted by The ISV Society, where Crestwood Associates, Avalara, and ADP will help you navigate the critical parts of this transition:

What’s different in Acumatica (and why it matters)
How to avoid compliance and tax headaches
Why aligning payroll, HR, and financials gives you a competitive edge

Whether you're deep in planning or just exploring what’s next, this session will give you clarity and actionable next steps.

Sign up today for this free workshop.
https://hubs.li/Q03LJVwx0

10/07/2025

Microsoft commissioned Consulting to conduct a Total Economic Impact™ study to find the ROI businesses can realize by deploying Microsoft Dynamics 365 Business Central. Check out the report to see what they found and then get in touch to see how we can help your business see similar results.

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