If you’re in charge of picking sales software for a B2B team, you know the drill—every vendor swears their tool will make your reps unstoppable. But when you cut through the hype, you mostly want to help your team close more deals, without drowning in features you’ll never use. This guide is for sales leaders, ops folks, and anyone stuck in the weeds of comparing “go-to-market” platforms like Octavehq with the rest of the pack.
Let’s get to the real questions that help you choose software that actually works for your business, instead of just checking boxes.
1. Get Clear on What Your Sales Team Actually Needs
Before you even open a demo tab, step back. What problem are you trying to solve? (And if you hear “digital transformation,” run.)
- Are you looking to speed up proposal creation?
- Is your pipeline tracking a mess?
- Are handoffs between marketing and sales dropping leads?
- Or are you honestly just tired of your reps complaining about the current tool?
Write down your top 3-5 must-haves. If you can’t do this, you’re just shopping for features you don’t need.
Pro tip: Ask a couple of your best (and worst) reps what’s slowing them down. You’ll get real answers and avoid buying shelfware.
2. Make a List of Real Contenders
“Go-to-market” software is a catch-all term. You’ve got everything from simple proposal tools to all-in-one sales platforms. Here’s how to build a shortlist:
- Start with your current pain points (from step 1).
- Look at tools in these buckets:
- Proposal/Quote tools: Octavehq, PandaDoc, Qwilr
- Sales engagement: Outreach, Salesloft
- CRM add-ons: HubSpot Sales, Salesforce CPQ
- All-in-ones: Apollo.io, Freshsales
Don’t get distracted by “market share” or “category leaders.” The biggest tools are often the most bloated and expensive.
Skip: Any vendor that hides their pricing or buries you in “custom solutions” before you even have a trial.
3. Dig Into the Features—But Ignore the Noise
Now the fun part: demos, feature lists, and sales pitches. Here’s how to cut through the clutter.
What Actually Matters
- Ease of use: How many clicks to send a proposal or update a deal?
- Integrations: Does it play nice with your CRM, email, and whatever else you’re using?
- Collaboration: Can multiple people edit, comment, or track changes in real time?
- Analytics: Do you get useful reports, or just pretty dashboards?
- Mobile access: Can your team do their job from their phone, without cursing?
What Usually Doesn’t
- Endless customization (you’ll never use half of it)
- AI this and AI that (unless you can see a real, working demo)
- Marketplace add-ons you’ll never touch
Pro tip: Ask for a real-life walkthrough—not a canned demo. “Show me how a rep would create, send, and get a proposal signed. Time it.”
When you look at a tool like Octavehq, see if it actually helps your team move faster—or just looks slick in a demo.
4. Test with Real Deals, Not Just Dummy Data
Most software looks great in a sandbox. The only way to know if it fits is to run a real deal or two through it.
- Set up a trial or pilot with your actual sales process.
- Have a few reps use it on real prospects.
- Watch for bottlenecks: Where do they slow down? Where do they cheat and go back to email or Excel?
- Ask for honest feedback—especially from the folks who usually grumble about new tools.
If the tool takes more training than your CRM, it’s probably not going to stick.
Skip: Any vendor that won’t let you trial the software with your own data. That’s a red flag.
5. Compare Costs—All of Them
Price is rarely as simple as a monthly fee per user. Here’s what to watch for:
- Base price: Is it transparent? Or do you need a sales call for a quote?
- Add-ons and upgrades: Are key features (e.g., e-signature, analytics) extra?
- Implementation fees: Is there a setup cost? Mandatory onboarding or training?
- Contract terms: Can you go month-to-month, or are you locked in for a year?
- Hidden costs: Will you need to hire a consultant just to get started?
Octavehq is usually priced mid-market, but always check if what you need is included in the base price. Some tools are deceptively cheap upfront but get you with “premium” features later.
If you’re comparing several options, make a simple spreadsheet. Stack up the real costs for 1 year, with everything included.
6. Check Vendor Support and Roadmap
No software is perfect. What matters is how the company responds when things break (and they will).
- Support: Is it chat, email, or a phone number? What’s the SLA?
- Onboarding help: Will they actually help you get up and running, or just throw you videos?
- Product roadmap: Are they shipping useful updates, or just chasing trends?
- Customer reviews: Look for consistent complaints about bugs, downtime, or support dead-ends.
You don’t want to be stuck with a vendor who disappears once you sign the contract.
Pro tip: Ask for references from companies your size and industry. If they can’t provide them, move on.
7. Look for Real Differentiators—Not Just Feature Parity
It’s easy to get lost in feature checklists. But what really makes one tool stand out?
- Unique workflow: Does the tool fit the way your team actually sells? Or are you bending your process to fit their software?
- Time to value: Does it help your reps get to “done” faster?
- Adoption rates: Will your team actually use it, or just keep working around it?
For example, Octavehq sells itself on making proposals fast and trackable. If that’s your top pain point, it could be a fit. But if you need deep pipeline analytics or complex quoting, it might fall short compared to something like Salesforce CPQ.
Ignore vendor claims about being “all-in-one” unless you see it in action. Most of the time, “all-in-one” means “jack of all trades, master of none.”
8. Make a Decision—Then Actually Roll It Out
Once you’ve picked your tool, don’t just toss it over the fence to IT or sales ops.
- Train your team (short sessions, real workflows, skip the fluff).
- Set a deadline for switching over—don’t let people straddle two systems for months.
- Track usage for the first 30-60 days. Are deals moving faster? Are reps using the tool, or finding workarounds?
- Be ready to adjust. If you made the wrong call, don’t be afraid to pivot.
Keep It Simple—And Iterate
Choosing sales software shouldn’t take months or require a PhD in feature comparisons. Get clear on what you need, see how real reps use it, and don’t overthink the bells and whistles. Most teams are better off with something simple that gets used every day, not a “platform” that collects dust.
There’s no perfect tool—just the right one for your current team and workflow. Test, launch, and if it’s not working, don’t wait to try something else. Your sales team (and your sanity) will thank you.