If you’re responsible for picking sales process software for a B2B team, you know the drill: every vendor claims their tool will “revolutionize” how you go to market. But you don’t need revolution—you need something that actually saves your team time, helps you close deals, and doesn’t break the bank (or your brain). This guide is for sales leaders, ops folks, and anyone who just wants to cut through the noise, compare Boomerang with the competition, and make a decision you won’t regret in six months.
Let’s get you a process that works—instead of a bloated tech stack and a pile of unused features.
Step 1: Get Clear on Your “Must-Have” Problems
Before you even look at Boomerang or any other B2B GTM (go-to-market) tool, get honest about what’s actually slowing down your sales team. Not what vendors say you should want—what your team needs fixed.
Ask yourself: - Where are deals falling through the cracks? - What’s eating up reps’ time? - Which manual tasks are making people groan? - Where do you have data gaps? - What’s not working with your current tools?
Write your answers down. You want specifics, not just “improve productivity.” (That’s a recipe for buying expensive shelfware.)
Pro tip: If you can’t list 3–5 core pain points, talk to your reps. They’ll have opinions.
Step 2: Know What Boomerang Is (and Isn’t)
Let’s cut through the marketing fluff. Boomerang is not a CRM, and it’s not an all-in-one sales platform. Its bread and butter is streamlining repetitive sales workflows—think scheduling, follow-ups, reminders, and automating those “did you see my last email?” nudges that keep deals moving.
Boomerang is good for: - Automating email follow-ups that otherwise get missed - Easy scheduling links for meetings (without 10 back-and-forths) - Simple reminders so prospects don’t fall off your radar
But Boomerang is not going to: - Replace Salesforce or HubSpot as your system of record - Do deep forecasting or pipeline analytics - Run your outbound sequences with complex branching logic
If your main pain points are around sales engagement, follow-ups, and keeping deals from dying of neglect, Boomerang is worth a look. If you need a full sales engagement platform or something to overhaul your CRM, it’s not the right tool—don’t let a slick demo convince you otherwise.
Step 3: Map Boomerang Against the Competition
Here’s where the rubber meets the road. Let’s say you’re considering Boomerang alongside tools like Outreach, Salesloft, Mixmax, or even basic calendar schedulers like Calendly. Don’t get distracted by flashy features—compare them on the problems you actually need solved.
Create a simple chart:
| Feature/Need | Boomerang | Outreach | Salesloft | Mixmax | Calendly | |--------------------------------------|-----------|----------|-----------|--------|----------| | Automated email follow-ups | ✔️ | ✔️ | ✔️ | ✔️ | ❌ | | Meeting scheduling | ✔️ | ✔️ | ✔️ | ✔️ | ✔️ | | Multi-channel sequences (calls, SMS) | ❌ | ✔️ | ✔️ | ❌ | ❌ | | Salesforce integration | Limited | Strong | Strong | Good | Basic | | Ease of use | Easy | Complex | Complex | Medium | Easy | | Price | $ | $$$ | $$$ | $$ | $ |
What this tells you: - If you want just email and calendar help, Boomerang or Mixmax can do the trick—without the complexity or cost of Outreach/Salesloft. - If you need heavy-duty sequence automation, call/SMS steps, and deep CRM integration, Boomerang won’t cut it. That’s Outreach/Salesloft territory (but expect a learning curve and a big bill). - Calendly is great for scheduling, but that’s it. No follow-up automation.
Ignore “AI” and buzzword features—unless you can tie them directly to your pain points. No one ever said, “We lost that deal because our tool didn’t have smart AI content recommendations.” Focus on the basics.
Step 4: Look Under the Hood—Usability and Adoption
A tool is only as good as your team’s willingness to use it. Fancy features mean nothing if your reps keep going back to Gmail and spreadsheets.
Ask: - How hard is it to set up? - Can someone non-technical use it after a 30-minute walkthrough? - Are there hidden hoops to jump through (IT approvals, complex integrations, etc.)? - What does onboarding/support actually look like?
Here’s the honest scoop: - Boomerang: Setup is fast, especially if you’re on Gmail or Outlook. Adoption is usually high because it works where reps already live (their inbox). - Outreach/Salesloft: Powerful, but expect a few weeks of onboarding and regular admin work. Some reps will resist the process-heavy interface. - Mixmax: Middle ground—more features than Boomerang, but can be overwhelming for non-techy folks. - Calendly: Dead simple, but limited scope.
Pro tip: Ask for a free trial and make a rep (or two) actually use the tool for a week. Don’t just watch a demo.
Step 5: Pricing and the “Total Cost of Ownership” Trap
Don’t just look at sticker price. Think about what you’re actually getting, and what hidden costs might pop up.
- Boomerang: Typically low monthly per-user cost. No big implementation fees. You’ll probably pay more if you want advanced features or enterprise support, but it’s straightforward.
- Outreach/Salesloft: Expensive, especially for small teams. Annual contracts are the norm. You might need a dedicated admin and extra budget for integrations.
- Mixmax: Middle of the road. More affordable than Outreach/Salesloft, but pricier than Boomerang for advanced plans.
- Calendly: Cheap for scheduling only.
Hidden costs to watch out for: - Training time (are you paying your team to “figure it out”?) - Integration headaches (does it actually play nice with your CRM?) - Change management (will you need to bribe reps to use it?)
Don’t get sold on a tool just because it’s “enterprise-grade.” If you’re a 10-person sales team, you don’t need the same setup as a Fortune 500 company.
Step 6: Beware of Feature Creep and Shiny Object Syndrome
It’s easy to get seduced by long feature lists. But most sales teams use about 10% of what their tools can do.
- Make a list of the core features you need (see Step 1).
- Ignore stuff that sounds cool but doesn’t solve an actual problem for your team.
- Ask vendors: “What do your most successful customers actually use the most?”
You’re looking for a tool that does a few things really well, not one that promises to do everything.
Step 7: Test with Real Deals, Not Just Dummy Data
The only way to know if a tool really streamlines your sales process is to use it on actual prospects. Set up a mini-pilot:
- Pick 2–3 reps (ideally, one tech-savvy, one tech-averse, one in the middle)
- Have them run their deal cycle using the tool for a week or two
- Ask them: What saved them time? What was annoying? What did they ignore?
If your team is still using their old workflows after the trial, that’s your answer—move on.
Step 8: Talk to Real Users, Not Just Reference Calls
Vendors will always connect you with their happiest customers. Go find your own references:
- Ask peers in your network what they don’t like about the tool.
- Search LinkedIn or Reddit for honest reviews (not paid testimonials).
- Pay attention to complaints about support, downtime, or “death by feature bloat.”
You’ll get a much more realistic sense of what it’s like to live with the tool day to day.
Step 9: Make Your Decision—Then Keep It Simple
Once you’ve done your homework, pick the tool that solves your real problems with as little fuss as possible. Don’t overcomplicate it.
Remember: - “Good enough and actually used” beats “perfect on paper but ignored.” - You can always add more tools later—don’t try to solve every possible sales process issue at once. - Keep your stack lean. The more tools, the more things break.
Keep It Simple and Iterate
Choosing sales process software isn’t about finding the “best” tool. It’s about finding the right fit for where your team is right now. Start small, focus on your must-have problems, and don’t be afraid to ditch a tool if it isn’t getting used. The simpler your stack, the more likely your team is to actually close deals—instead of wrestling with software.
Remember: Solve real problems, ignore the hype, and make life easier for your reps. That’s how you actually move the needle.