If you’re in charge of picking sales software, you know the drill: endless demos, big promises, and half the tools end up gathering dust. This guide is for sales leaders, ops folks, or anyone sick of chasing shiny objects and looking for real results. We’ll walk step-by-step through how to evaluate B2B go-to-market (GTM) tools like Hothawk so your team actually closes more deals — not just adds another tab to Chrome.
1. Get Clear on What You Actually Need
Before you even look at a tool, grab a notepad and jot down what’s broken right now. Is your pipeline a black box? Reps spending more time updating CRM than selling? Leads slipping through the cracks? Be brutally honest.
Common needs to clarify: - Pipeline visibility: Do you know what deals are real, or is everyone guessing? - Lead management: Are good leads getting lost or mishandled? - Reporting: Are you spending hours in spreadsheets just to answer simple questions? - Rep productivity: Are your reps bogged down in admin work? - Account targeting: Is your team focused on the right accounts, or just taking shots in the dark?
Pro tip: The more specific your pain points, the easier it is to cut through vendor noise later.
2. Make a Short List — Ignore the Hype
Every week, there’s a new “AI-powered” GTM platform promising to double your pipeline. Most of it’s marketing fluff.
How to build a focused shortlist: - Talk to peers: What are similar teams actually using (and still using after a year)? - Check real reviews: Ignore “sponsored” analyst reports. Look for reviews after 6+ months of use. - Prioritize integration: If it doesn’t play nice with your CRM and email, skip it. - Filter by must-haves: Go back to your pain points and cut anything that can’t solve them.
You’ll probably end up with 3–5 real contenders. That’s plenty.
3. Dig Into the Demos — Ask the Awkward Questions
Now comes the parade of demos. Don’t let slick slide decks distract you.
What to focus on in demos: - Real workflows: Ask to see how a rep would use the tool in a typical day. Not a cherry-picked “happy path.” - Data in, data out: How does it get your existing data in? How do you get it out if you leave? - Setup time: How long to get your team up and running, really? (Ask for customer references if they claim “one day.”) - Failure modes: What happens if something breaks, or your CRM changes? - Hidden costs: Is there a “basic” plan that’s actually useless? What’s extra?
Pro tip: Ask: “What’s the most common reason customers leave?” If the rep dodges, that’s a red flag.
4. Test Drive With Real Data — Not Just a Dummy Sandbox
A week in a fake demo environment tells you nothing. Push for a real pilot, ideally with your own data and at least a couple of your actual reps.
What to look for during a pilot: - Adoption: Are reps using it without constant hand-holding, or is it a chore? - Time to value: How long before you actually see something useful? If it’s weeks, that’s a problem. - Accuracy: Is the tool’s data clean, or does it spit out garbage you need to double-check? - Customization: Can you tweak it for your sales process, or is it “our way or the highway”? - Support: How fast do you get real answers, not just knowledge base articles?
If the vendor won’t give you a real pilot, ask yourself why.
5. Examine Integration and Data Ownership
This is where a lot of tools fall down. It’s great if a tool “integrates” — but does it actually sync data, or just import/export CSVs? And who owns your data if you leave?
Key questions: - Bidirectional sync: Does it push and pull data from your CRM in real time? Or are you stuck “reconciling” things manually every week? - APIs and access: Can your ops team work with the data, or is it a black box? - Data export: Can you take all your account and activity data with you if you switch tools? - Security: Is their security page more than just a badge? Ask for specifics.
Don’t trust vague answers — get a real walkthrough or documentation.
6. Calculate the Real Cost (Not Just the Sticker Price)
B2B software pricing is a maze. Watch for add-ons, per-seat “gotchas,” and the classic “implementation fee” surprise.
What to factor in: - License tiers: Is the base tier useless? What features require an upgrade? - Implementation: Is setup included, or extra? Who’s actually doing the work? - Training: Will you need to pay extra to get your reps up to speed? - Support: Is “premium” support just code for “actually helpful”? - Contract terms: Can you get out after 6 months, or are you locked in for a year+?
Pro tip: Ask for a full quote, including any “optional” add-ons you’ll realistically need. Don’t be afraid to walk if they can’t be clear.
7. Get Buy-In From the Team — Early
It’s tempting to push a tool from the top down. Don’t. If your reps hate it, adoption will tank, and you’ll be back at square one.
How to build buy-in: - Involve power users: Get a few trusted reps and ops folks in the evaluation early. - Show, don’t tell: Let them try the tool and give honest feedback. - Highlight quick wins: What will save them time this quarter, not just “in theory”? - Address skepticism: Be honest about what the tool won’t do. Better to underpromise than overhype.
If the team’s lukewarm or outright hostile, listen. It probably means the tool’s not a fit, or you need to rethink how you’re rolling it out.
8. Ignore These Features (Unless You Really Need Them)
Vendors love to throw in bells and whistles. Most of it just clutters the UI and confuses users.
Features to skip unless you have a concrete need: - “AI” everything: Unless it plugs into your workflow and saves real time, ignore the buzzword. - Gamification: Unless you have a team that loves leaderboards, this usually just annoys adults. - Social integrations: If your sales motion isn’t on LinkedIn, you don’t need a LinkedIn widget. - “Predictive” anything: Most predictions are just fancy charts. Unless you can act on them, skip it.
Stick to what fixes your pain points. The rest is just noise.
9. Make the Call — and Set a 90-Day Check-In
Once you decide, rip off the Band-Aid and commit. But set a clear 90-day review: is the tool delivering real value, or just more admin?
How to run a post-implementation gut check: - Are reps still using it? If not, why? - Has reporting gotten easier, or just different? - Are your original pain points fixed, or just shifted around? - Can you adjust, or do you need to pull the plug?
Most sales teams stick with tools far too long out of inertia. Don’t be afraid to change course if it’s not working.
Keeping your sales stack simple is a superpower. Most teams win or lose deals because of people and process, not software. Use this guide to cut through the noise, pick tools that solve real problems, and don’t be afraid to try, tweak, or toss what doesn’t work. Your team (and your budget) will thank you.