Path to Head of Sales / SLT
Location: Canada / Remote
Comp: $100k+ base + above-market commission + meaningful equity (5–10% earn-in)
About Cloudloop
Cloudloop is a consulting and delivery partner focused on complex, regulated environments.
We work at the intersection of cloud platforms, DevOps, Salesforce, and digital transformation,
helping organizations modernize safely, reduce operational drag, and actually ship.
Our clients span MedTech, life sciences, financial services, and other highly regulated industries.
We don’t sell slide decks; we build and operate real systems in production.
We’re now at an inflection point: platform, DevOps, and cloud-led work is becoming a first-class growth engine
for the company. We’re looking for the person who will build that revenue motion from the ground up.
The Role
This is not a traditional AE role.
You are our first dedicated platform seller and a future Head of Sales / SLT member.
You’ll start as a player-coach: selling, shaping the GTM motion, and helping define how Cloudloop brings platform,
DevOps, and Salesforce-adjacent work to market.
You’ll work closely with Cloudloop leadership, delivery leads, and senior engineers to turn what we already do well
into a repeatable, scalable revenue engine.
What You’ll Do
Build & Own Platform GTM
- Own new revenue across Platform Engineering, DevOps, Cloud, and Salesforce-adjacent architecture
- Define ICPs, deal shapes, pricing models, and qualification standards
- Translate technical delivery into clear commercial value for buyers
- Lead early pipeline creation through outbound, partner motion, and relationships
Sell Complex, Real Work
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Sell services-led platform engagements: cloud modernization, DevOps automation, FinOps, security,
compliance-aware architecture, and Salesforce platform integrations
- Navigate long, multi-stakeholder sales cycles in regulated environments
- Partner with technical leadership during discovery and solutioning
Shape the Practice
- Provide feedback into service packaging and delivery standards
- Influence hiring priorities as the practice scales
-
Help determine where Salesforce fits best as part of a broader platform story
(not as a standalone pitch)
Grow Into Leadership
- Hire and mentor additional sellers as revenue matures
- Transition into Head of Sales / CRO responsibilities
-
Join the Senior Leadership Team, contributing to strategy, forecasting, and company direction
What You Bring
We’re looking for someone who has done this before, even if informally.
Experience
- 7+ years selling technical services or platform-led solutions
- Proven success selling into regulated or high-complexity environments
-
Comfort selling work that spans:
- Cloud platforms (AWS and/or Azure)
- DevOps & Platform Engineering
- Security, compliance, and operational maturity
- Salesforce as part of a broader ecosystem
- Experience building pipeline without relying solely on inbound leads
How You Work
- You understand engineers and can sell with them, not over them
- You’re comfortable with ambiguity and early-stage GTM
- You think in systems, not just deals
- You want ownership, not just quota
Bonus Points
- Background in consulting or technical delivery
- Familiarity with Salesforce platform architecture and integrations
- Experience building or scaling a sales function
- Interest in shaping culture and mentoring others
Compensation & Growth
This role is designed for someone who wants upside and ownership, not just OTE.
- $100k base salary
- Above-market commission on new platform revenue
- Meaningful equity (5–10%), structured as an earn-in tied to milestones
-
Clear, intentional path to:
- Head of Sales / CRO
- Senior Leadership Team membership
- Long-term value creation and exit participation
Why This Role Is Different
- You’re not inheriting a rigid sales machine — you’re helping build it
- You’ll have direct access to leadership, delivery teams, and company financials
- You’ll shape how Cloudloop grows, not just what it sells
- Your success directly influences the company’s future structure and leadership
Sound Like You?
If you’re a platform-minded seller who’s tired of selling someone else’s roadmap — and you want to help build
something real, durable, and technically honest — we should talk.
Interested? Reach out at [email protected]
