When to Upgrade from a Simple CRM to an Advanced CRM: A Strategic Approach

Cus­tomer Rela­tion­ship Man­age­ment (CRM) soft­ware has come a long way. Many paint­ing com­pa­nies start by man­ag­ing leads and clients in spread­sheets before tran­si­tion­ing to a sim­ple CRM like Pipeline CRM, Job­ber, or oth­ers. Oth­ers, espe­cial­ly younger com­pa­nies, jump into CRM sys­tems right away, while long-estab­lished busi­ness­es might be oper­at­ing on old­er, frag­ment­ed sys­tems. But when does it make sense to upgrade from a sim­ple CRM to a more advanced, auto­mat­ed sys­tem like Hub­Spot, Sales­force, or GoHigh­Lev­el? And more impor­tant­ly, how do you ensure your team is ready for the transition?

The Pros of Using a CRM (Even a Sim­ple One)

Many com­pa­nies start with spread­sheets or basic CRMs, and that’s a good first step. Here’s why any CRM is bet­ter than no CRM:

• Cen­tral­ized Data – Keeps all cus­tomer and prospect infor­ma­tion in one place.
• Task and Fol­low-Up Track­ing – Ensures no leads fall through the cracks.
• Pipeline Vis­i­bil­i­ty – Shows where poten­tial jobs are in the sales process.
• Basic Automa­tions – Sends reminders and fol­low-ups automatically.
• Easy to Use – Sim­ple CRMs are designed to be intu­itive for teams.
• Lead Source Track­ing – Under­stand where leads are com­ing from, allow­ing for bet­ter mar­ket­ing decisions.
• Job Sales & Rev­enue Track­ing – Track when jobs are sold and their val­ue, help­ing mea­sure cost per lead, cost per sale, and over­all sales performance.

It’s impor­tant to note that less expen­sive or sim­ple CRMs typ­i­cal­ly lack robust automa­tion fea­tures. That’s what you’re pay­ing for when you move to Hub­Spot, Sales­force, or GoHigh­Lev­el—the abil­i­ty to cre­ate pow­er­ful fun­nels, work­flows, and automa­tion that save time and dri­ve effi­cien­cy. The more you can auto­mate, the bet­ter — but only when the time is right. If you’re just start­ing out, max­i­mize what you have. How­ev­er, once your busi­ness is grow­ing rapid­ly and becom­ing more com­plex, an advanced CRM with automa­tion becomes a necessity.

For com­pa­nies just start­ing out or with rev­enue up to $2.5M, a tool like DripJobs can be a great option. It requires min­i­mal learn­ing, is designed specif­i­cal­ly for con­trac­tors, and helps stream­line esti­mates, invoic­es, and fol­low-ups. Many busi­ness­es have excelled with DripJobs, but as a com­pa­ny grows and needs more advanced automa­tion, it may even­tu­al­ly be time to explore high­er-tier CRMs.
If you’re using a sim­ple CRM effec­tive­ly, it can work well for busi­ness­es up to $2.5M – $4M in rev­enue. Tools like Pipeline CRM and Job­ber pro­vide essen­tial CRM func­tions with an easy-to-use inter­face, mak­ing them ide­al for com­pa­nies just get­ting start­ed with sales management.

When Do You Need to Upgrade to a More Advanced CRM?
A more advanced CRM (Hub­Spot, Sales­force, GoHigh­Lev­el, Pipedrive, etc.) makes sense when:

1. Your Sales Team Has Out­grown the Sim­ple CRM
   • If you find that your sales team needs bet­ter report­ing, advanced automa­tion, or a more struc­tured sales process, a more pow­er­ful CRM may be necessary.
   • If your team isn’t ful­ly using your cur­rent CRM, how­ev­er, push­ing them to use all its fea­tures first is a smarter move before upgrading.
2. You Need Advanced Automa­tion & Lead Nurturing
   • Tools like Hub­Spot and GoHigh­Lev­el allow for sophis­ti­cat­ed email cam­paigns, text fol­low-ups, and lead track­ing beyond what sim­ple CRMs offer.
   • Auto­mat­ed work­flows can save time, increase con­ver­sions, and ensure every lead is fol­lowed up with properly.
3. You’re Run­ning Mul­ti­ple Soft­ware Sys­tems That Don’t Com­mu­ni­cate Well
   • Many old­er paint­ing com­pa­nies use a mix of dis­con­nect­ed apps: Quick­Books, Smartsheet, Com­pa­ny­Cam, esti­mat­ing tools (PaintScout, Esti­mate Rock­et), and others.
   • A more advanced CRM helps cen­tral­ize and inte­grate these tools, reduc­ing data silos.
4. You Want Bet­ter Sales & Mar­ket­ing Integration
   • Advanced CRMs con­nect mar­ket­ing automa­tion with sales pipelines, ensur­ing leads from Google Ads, Face­book, or direct mail flow direct­ly into a sys­tem that nur­tures and tracks them.
5. Your Busi­ness is Scal­ing Rapid­ly ($4.5M+ in Revenue)
   • If your team is grow­ing and you have mul­ti­ple sales­peo­ple han­dling leads, an advanced CRM pro­vides bet­ter report­ing, fore­cast­ing, and team col­lab­o­ra­tion tools.

Before You Upgrade: Max Out Your Exist­ing CRM

Switch­ing to a new CRM is not a mag­ic bul­let. Many com­pa­nies jump to Hub­Spot or Sales­force only to real­ize their sales team isn’t ful­ly using the CRM they already had.
Instead, take these steps first:

1. Get Your Sales Team Com­mit­ted – Ensure your team is using all avail­able fea­tures of your cur­rent CRM. Set goals, track adop­tion, and pro­vide coaching.
2. Iden­ti­fy Pain Points – Is your CRM tru­ly lim­it­ing your sales process, or is the issue team dis­ci­pline and execution?
3. Track ROI – Are you los­ing leads or miss­ing out on oppor­tu­ni­ties due to CRM lim­i­ta­tions? If so, it might be time to upgrade.
4. Test Small Automa­tions First – Before jump­ing into a $50K+ Hub­Spot set­up, try small automa­tion tools (Zapi­er, Mailchimp, etc.) to see if you real­ly need a full-fledged system.

Com­pa­nies That Can Help with CRM Inte­gra­tion
If you do decide to upgrade, it’s essen­tial to work with pro­fes­sion­als who know how to inte­grate sys­tems effec­tive­ly. Boolean is one such com­pa­ny that spe­cial­izes in Hub­Spot, Airtable, and oth­er soft­ware inte­gra­tions. They can help you con­nect tools like Quick­Books, esti­mat­ing soft­ware, and your CRM to cre­ate seam­less work­flows. It is an invest­ment that requires a com­mit­ment on your end, but their exper­tise ensures that your set­up is done cor­rect­ly and efficiently.

Some paint­ing com­pa­nies pre­fer ​“all-in-one” solu­tions like Job­Tread, which con­sol­i­dates mul­ti­ple busi­ness func­tions in one plat­form. Oth­ers opt for a hybrid set­up, using tools like WorkGlue, Quick­Books, and PaintScout, ensur­ing all apps work togeth­er smooth­ly. The key is to find soft­ware that saves time, elim­i­nates redun­dan­cy, and improves effi­cien­cy — so you can focus on what you do best: paint­ing properties.

How to Plan for an Upgrade

If you decide an upgrade is nec­es­sary, don’t rush the process. A CRM switch can be dis­rup­tive, so take a strate­gic approach:

• Bud­get Wise­ly – Don’t just look at the soft­ware cost; fac­tor in train­ing, imple­men­ta­tion, and poten­tial downtime.
• Set a Time­line – Define when you’ll tran­si­tion and how you’ll roll it out.
• Get Buy-In from Your Team – Make the tran­si­tion excit­ing and aligned with com­pa­ny val­ues, rather than a forced change.
• Test Before a Full Switch – Many CRMs offer free tri­als or phased implementations.
• Ask Fel­low Paint­ing Con­trac­tors – Reach out to oth­ers in your indus­try with sim­i­lar-sized busi­ness­es. You can con­nect through paint forums, Face­book groups, indus­try asso­ci­a­tions like PCA or CPIA, and peer groups to learn from their expe­ri­ences before mak­ing a decision.

Switch­ing to a high-lev­el CRM when you’re already run­ning a busy, grow­ing com­pa­ny is not a sim­ple plug-and-play change. It requires care­ful plan­ning, invest­ment, and team buy-in to make it suc­cess­ful. Upgrad­ing too soon or with­out a plan can cause delays, frus­tra­tion, and wast­ed money.

Con­clu­sion: Work What You’ve Got Before You Upgrade

A more advanced CRM can be a game-chang­er—but only if your team is ready for it. If your sales­peo­ple aren’t ful­ly using your cur­rent sys­tem, don’t expect a new one to fix that prob­lem. Instead, set clear goals, coach your team, and track adop­tion. Then, when the time is right, upgrade strate­gi­cal­ly — on your terms, with a plan, and for the right rea­sons.
Need help decid­ing if it’s time for an upgrade? Let’s talk through your CRM set­up and build a plan that makes sense for your business.