If you're running sales, marketing, or revenue operations at a mid sized company, you know the pain: there are a thousand tools promising to "transform" your go-to-market motion. Most sound the same. Most don't work as advertised. And most take way more time to implement than anyone tells you up front. This isn't a list of the "top 10 tools"—it's a no-nonsense guide to actually figuring out what kind of software you need, how to cut through the hype, and how to make a decision you won't regret in six months.
This is for folks who have to live with the tools they pick. If you're tired of "innovation theater" and just want to get things done, read on.
Step 1: Get Clear on Your Actual Problems
Before you even look at a software comparison site, write down the real problems you're trying to solve. Not high-level fluff like “improve sales efficiency”—get specific:
- Are reps wasting time re-entering leads?
- Are you missing out on key accounts because you can’t see where deals are stuck?
- Is marketing sending leads the sales team ignores?
Pro tip: Ask the people doing the work. What’s annoying them every day? Skip the C-suite wishlist and focus on what’s actually slowing teams down.
What to Ignore
- “AI-powered” anything unless you can see exactly how it helps your team do less busywork.
- Tools that promise to “do it all” (they never do).
- Fancy dashboards you’ll look at twice.
Step 2: Map Your Existing Stack (Warts and All)
You don’t need a beautiful Visio diagram—just make a list of what you’re using now. Include:
- CRM (like Salesforce, HubSpot)
- Marketing automation (Marketo, Pardot, etc.)
- Sales engagement (Outreach, Salesloft)
- Data enrichment, intent tools, analytics, all the bolt-ons
Jot down:
- What’s working
- What’s a pain to use
- Where you’re double-entering data or losing info
Why bother? You need to know what has to play nicely together, or you’ll buy something that breaks your workflow and makes things worse.
What to Ignore
- Integrations you might want someday.
- The hope that “this time we’ll finally use all the features.”
Step 3: Set Non-Negotiables (and Nice-to-Haves)
It’s tempting to want everything, but you’ll just end up with shelfware. Divide your wish list:
Must-Haves:
- Integrates with your CRM out of the box (no, Zapier doesn’t count for core data)
- Can be configured by someone on your team (not just a consultant)
- Actually solves one of the painful problems from Step 1
Nice-to-Haves:
- Fancy reporting
- Built-in templates or playbooks
- “AI” features that look interesting but aren’t critical
Write these down. When you demo tools, check off only the “must-haves.” If a vendor can’t nail those, move on.
What to Ignore
- Roadmap promises (“That’s coming next quarter!” means “maybe, someday”)
- “Best practices” features that don’t fit how your team works
Step 4: Make a Shortlist—But Keep It Short
This is where most people waste time. You don’t need to demo 10 tools. Three is plenty. Use review sites (G2, TrustRadius) and ask peers in similar companies. Don’t get dazzled by category leaders if they’re built for companies twice your size.
A few tools you’ll run into:
- Sales engagement: Outreach, Salesloft, Groove
- Revenue intelligence: Gong, Chorus
- Go-to-market orchestration: Discolike, LeanData, Chili Piper
Look for tools aimed at mid sized companies (not just “enterprise-ready”), and skip the ones that clearly target huge, complex orgs.
Pro tip: If the vendor can’t explain their pricing on the first call, or you need to talk to “someone else” for a quote, that’s a red flag for mid sized businesses.
What to Ignore
- “Magic quadrant” rankings—they’re pay-to-play and tell you nothing about fit.
- Endless feature checklists.
Step 5: Run Realistic Demos (No Fluff)
Don’t let vendors run a slick demo you’ll never reproduce. Before the call, send them 2-3 scenarios based on your actual workflow. For example:
- “Show me how a lead from web chat gets routed to the right rep.”
- “Walk through syncing a closed-won deal to our CRM, including custom fields.”
- “How do I fix a sync error if data doesn’t match up?”
Make them use your data (even if it’s fake). If they can’t, that’s telling.
Ask the tough questions:
- How long does setup really take—not “in a perfect world”?
- What does your support look like after launch? (Ask for real examples.)
- Can we configure this ourselves, or do we need paid services?
Warning signs:
- “You’ll need to upgrade for that feature.”
- “We recommend our professional services team for implementation.”
What to Ignore
- Demos that use “test” accounts or canned data that doesn’t match your world.
- Promises of “white glove onboarding” that cost extra.
Step 6: Check the Hidden Costs and Gotchas
The sticker price is almost never the whole story. Dig in:
- Are there mandatory onboarding fees?
- Does the price jump if you add users or hit a data limit?
- Are integrations included, or do you pay extra?
- How do they handle contract renewals?
Pro tip: Ask for a sample contract and SOW (Statement of Work) before you commit. The fine print is where most mid sized companies get burned.
What to Ignore
- “Introductory pricing”—assume you’ll pay more next year.
- “Unlimited” plans that turn out to have fair use caps.
Step 7: Pilot with Real Users (Not Just Admins)
If possible, run a trial or pilot with 2-3 reps or marketers who’ll use the tool every day. Watch for:
- Where they get stuck or frustrated
- If they find real shortcuts, or just new workarounds
- Whether they actually want to keep using it
Don’t just rely on admin feedback. The people entering leads, making calls, or sending campaigns will tell you fast if the tool is a help or a hassle.
Pro tip: Set a deadline for your pilot. If you don’t see value in 30 days, move on.
What to Ignore
- Vendor “success stories” that don’t match your business model.
- Internal “change champions” who love new tech but don’t do the actual work.
Step 8: Decide, Roll Out, and Watch Closely
Once you pick, keep rollout simple. Don’t try to automate everything on day one.
- Start with one team or process
- Get feedback quickly
- Make tweaks—don’t force-fit your old process if the new tool is better
Check in with users weekly at first. If adoption stalls, dig in: is it a training issue, or is the tool just not a fit?
Pro tip: Plan for what happens if you need to rip the tool out. Can you get your data back? Will you be locked in for years? Negotiate these points up front.
Wrap Up: Keep It Simple, Stay Sane
Choosing go-to-market software for a mid sized business isn’t glamorous, and it shouldn’t be a months-long process. Get clear on your problems, ignore the hype, and don’t fall for features you don’t need. If you keep things simple and listen to the people actually using the tools, you’ll make a choice that works in the real world—not just on a slide deck.
Iterate as you go. You can always swap tools later, but you’ll never get back the hours lost to a bad fit. Stay skeptical, stay practical, and trust your gut.