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Alessandra S.
Expert-Vetted

Alessandra S.

Fractional CMO | Client Strategy | Revenue, Retention & Growth

I take a direct approach to stalled growth, weak retention, and the hidden friction that makes businesses harder to scale than they should be. If growth has slowed or stalled, the problem is rarely effort. More often, it is weak funnels, mismatched positioning, unclear offers, underperforming follow-up, poor handoffs, CRM drag, or too much activity with too little commercial return. I help growth-focused companies find what is actually slowing momentum, then fix the right things first. You will get a clear view of what is working, what is not, and what needs attention now. For clients who want a sharp starting point, I offer a Revenue Leak Snapshot: a focused review of one offer, funnel path, customer journey, or follow-up system to uncover missed conversions, weak handoffs, and the highest-value next moves. Most clients start here. You get a clear breakdown of where performance is breaking and what to fix first, not a long report that sits untouched. In addition I can step in as your Fractional CMO and senior client strategy consultant. I have 15+ years of experience across SaaS, logistics, ecommerce, nonprofit, fintech, and other growth-focused businesses. My work sits across revenue growth, retention, lifecycle marketing, CRM, marketing operations, and AI where it actually improves speed, clarity, and execution. I build the systems underneath growth: cleaner processes, stronger funnels, sharper follow-up, and, where useful, AI-supported workflows that improve productivity without adding noise. Sometimes the issue is weak positioning attracting the wrong leads. Sometimes retention slips because the follow-up and customer journey are underbuilt. Sometimes the CRM and automation stack is underused, overcomplicated, or quietly working against the team. And sometimes it is simpler: too many moving parts, not enough clarity, and no one fixing the actual source of the drag. I don’t mistake activity for strategy. I build the structure underneath growth so the business is not forever improvising its way through the same problems. Recent results: • 333% increase in qualified leads for a SaaS company • 47% revenue lift for a B2B firm • 40% increase in leads • 24% improvement in conversion following a strategic repositioning initiative I’ve worked deeply with HubSpot, Pardot, Marketo, Eloqua, and SharpSpring — from platform selection through implementation, training, and execution. Clients value that I can see the strategic picture and still get into the operational detail when needed. One described me as having “a foot in both the marketing and technology camps.” Another noted my “laser focus on delivering customer value.” I work best with companies that want clarity, traction, and less performative nonsense. When growth has become muddled, execution is not matching ambition, or the business has outgrown guesswork, I help make growth make sense again.

🇨🇦Vancouver, Canada$199/hr100% JSS4.65 (24)Since Dec 2013
GlobeUpwork

Earnings and projects

MRR
$3.7k

Last 6 months ÷ 6

World#9,048 / 412k
🇨🇦Country#251 / 7,133
Revenue, last 30 days
$9.1k

Last 6 months: $22k

World#1,766 / 412k
🇨🇦Country#68 / 7,133
Total earnings
$235k

Billed in all: $263k

World#11,802 / 412k
🇨🇦Country#296 / 7,133
Per project
$6.7k

$4.5k in the last 6 months

World#25,465 / 412k
🇨🇦Country#434 / 7,133
Projects, last 6 months
5
80% fixed20% hourly
World#41,746 / 412k
🇨🇦Country#656 / 7,133
Projects in all
35

Across 43 contracts

49% fixed51% hourly
World#85,277 / 412k
🇨🇦Country#1,557 / 7,133

Earnings, last 30 days

$263k+$9.1k earned in the last 30 daysBilled in all, before Upwork's fee · drag across the chart to see what was earned in any stretch
$250k$255k$260k$265kOct 8Oct 23Nov 7

Skill rankings: Top 1% in Content Writing

Ranked by MRR among everyone on Upwork with the skill.

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  3. #88Presentations3,455 freelancers · 🇨🇦 #9Top 3%
  4. #119Customer Relationship Management5,121 freelancers · 🇨🇦 #5Top 2%
  5. #139Presentation Design6,690 freelancers · 🇨🇦 #7Top 2%
  6. #140B2B Marketing4,592 freelancers · 🇨🇦 #6Top 3%
  7. #289Content Writing23,842 freelancers · 🇨🇦 #6Top 1%
  8. #292Marketing Strategy8,415 freelancers · 🇨🇦 #7Top 3%