{"id":685477,"url":"https://alion.io/job/contactmonkey-scaled-customer-success-lead","title":"Scaled Customer Success Lead","company":{"id":674782,"name":"ContactMonkey","domain":"contactmonkey.com","url":"https://alion.io/company/contactmonkey","size_band":"5000+","is_staffing_agency":false,"employer_type":"direct","is_intermediary":false,"listed_via":null,"ats_vendor":"Greenhouse","truth_index":null},"role":"Customer Success","role_family":"Customer Success","seniority":"lead","employment_type":null,"work_mode":"hybrid","remote_scope":null,"remote_scope_basis":null,"remote_working_hours":null,"hiring_geo_confidence":"structured","locations":["Toronto, Canada"],"countries":["CA"],"hiring_countries":[],"hiring_countries_total":0,"salary":null,"salary_estimate":{"min_usd":34000,"max_usd":99000,"period":"year","method":"role_seniority_country_remote_cell","sample_n":17},"experience_years_min":5,"visa_sponsorship":false,"relocation_package":false,"has_equity":true,"technologies":[{"name":"Salesforce","optional":false},{"name":"Gmail","optional":true},{"name":"Outlook","optional":true}],"status":"live","first_seen_at":"2026-07-10T18:33:37Z","employer_posted_date":"2026-10-05","last_verified_at":"2026-10-21T03:28:36Z","board_verified":true,"closed_at":null,"days_open":102,"trust":{"level":"stale","repost_count":0,"flags":["stale"],"days_open":101},"description":"Hey there! We’re ContactMonkey\nOur mission? To power measurable employee engagement worldwide. And we’d love for you to join us!\nAbout the job -Scaled Customer Success Lead\nJoin our Customer Success team in a net-new, high-impact IC role where you will work to solve this problem: How can we use data, automation and AI to manage our SMB customer relationships at scale? As our Scaled Customer Success Lead, you won't just drive retention and GDR at the segment level. You’ll develop a deep understanding of the customer journey and lead in building the tech-touch motion behind it, from automations and health signals to AI-assisted workflows, proactive outreach, and scaled engagement.\nYou'll report to Sydney Pearson, our Director of Customer Success, and partner closely with Customer Success, Product, Marketing, and Sales Operations to build an SMB program that's as streamlined as it is effective.\nThis role is ideal for someone who has personally built and run a scaled CS motion before, someone who thinks in process and systems, acts on data, and knows how to keep a large, diverse book of business healthy without manual hand-holding on every account. A hands-on builder with strong ops and automation instincts, and fluency with AI tools.\nYour impact\nDesign and execute the tech-touch motion: automated onboarding sequences, usage-triggered nudges, health-based alerts, and scaled business reviews\nOwn customer retention (GDR) as your primary metric, the health and retention of the SMB segment globally is your responsibility\nOperate, extend, and iterate the existing customer health scoring and early-warning system that surfaces at-risk accounts before they reach the cancellation window\nLead churn diagnosis for the segment, maintain a data-backed, documented picture of why SMB accounts leave, and turn those insights into playbook improvements and feedback for the broader team\nDrive customer communications at scale, proactive, segmented outreach so no account goes dark\nBuild and iterate AI-assisted workflows, including business review generation, account risk summaries, and reactivation sequences\nOwn and refine automated segment health reporting to CS leadership\nWork cross-functionally with Product, Marketing, Sales, and Support to surface customer insights and close gaps that impact segment retention\nAbout you\n5+ years of experience in Customer Success or Customer Operations\nDirect experience owning a GDR/NDR outcomes, as the main point of contact, including renewals, upsell conversations, and account escalations\nDirect experience building and executing a scalable, low-touch CS motion\nRecent experience at an early-stage SaaS business\nInstrumented CS health and risk on a CS platform (Gainsight, Vitally, ChurnZero) or a homegrown stack (Salesforce + product analytics + automation)\nComfortable with Salesforce, Pendo, Gong, or equivalent tools to instrument health, productivity, and risk\nAble to generate your own reporting and insights without waiting on an analyst\nHow you can stand out\nExperience with AI tools that streamline workflows and improve the customer journey\nWhat we bring to the table \n100% employer-paid benefits + a Health Spending Account from day one\nWork from anywhere in the world for up to 4 weeks\nStock option plan-own a piece of our success\nRRSP Group Savings Plan to plan for your future\nGenerous vacation package to recharge and relax\nPersonal development budget to fuel your growth\nOne personal day + two volunteering days to give back\nYour Birthday off-celebrate on us!\nFive health days per year to stay at your best\nBeautiful downtown Toronto office for hybrid work-fully stocked with all the best snacks\nCompensation & Work Details\nThe salary range for this role is $120,000-$130,000 CAD + variable. Compensation is thoughtfully determined based on your experience, skill set, and alignment with our internal compensation framework and internal equity.\nWe’re always happy to answer questions about compensation throughout the hiring process.\nThis is a new position based out of our downtown Toronto office, at King and Spadina. Our team works in the office 3x per week to promote collaboration.\nWho We Are \nImagine being part of a team of brilliant minds, all shaping the future of workplace communication. Here at ContactMonkey, we’re not just sending out traditional emails with our internal comms software; we’re changing the way companies connect and communicate with their people. Brands like IKEA, Roku, KMPG, and countless others are using our solution to transform employee engagement.\nOur all-in-one platform-featuring a drag-and-drop email builder, engagement tools, and analytics-makes it easy for businesses to create, send, and measure their internal email campaigns directly within Outlook or Gmail. This way, internal communications go from being ignored to binge-worthy, sparking more opens, clicks, and conversations.\nWe’ve been on an explosive growth streak over the past few years, and we’re not slowing down anytime soon. Here’s a bit of what we’re proud of:\nRanked by the Globe & Mail as one of Canada’s fastest-growing companies\nRecognized in 2023, 2024 and 2025 Deloitte Technology Fast 50™ awards for revenue growth over the past four years\nRecognized in 2023, 2024 and 2025 Deloitte Technology Fast 500™ as one of the fastest-growing companies in North America\nRaised $55 million Series A financing in 2023\nDiversity is our strength\nAt ContactMonkey, we are building diverse products and we need a diverse team to do that. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status. \nWe are committed to creating an accessible experience for all candidates. If you require any accommodations or adjustments during the interview process or beyond, please inform us, and we will work with you to ensure the necessary support is in place. We are continually striving to enhance our accessibility practices and welcome any feedback or suggestions on how we can better serve candidates with accessibility.\nAI Disclosure: \nWe use AI to take notes during our interview. Applications and interviews are reviewed by our Talent Acquisition team. Our applicant tracking system utilizes AI for workflows and hiring process efficiencies.","description_format":"text","description_chars":6330,"description_truncated":false,"requirements":{"experience_years_min":5,"management_years_min":null,"team_size_min":null,"manages_managers":false,"education":null,"security_clearance":false,"languages":[]},"benefits":["Equity","Generous vacation","Hybrid work"],"hiring_locations":[{"name":"Canada","iso":"CA","kind":"country"}],"hiring_excludes":[],"relocation_offered":false,"industries":["Email Marketing","Team Communication & Collaboration"],"lifecycle":[{"event":"open","at":"2026-09-11T00:12:34Z"}],"visa":[],"liveness":{"score":12,"band":"cold","label":"Long shot","p_open":1,"p_active":0.428,"p_room":0.28,"age_days":101,"expected_fill_days":22,"reasons":["conf:3","win:tail","crowd:"],"computed_at":"2026-10-20T05:45:00Z"},"pay":null,"html_url":"https://alion.io/job/contactmonkey-scaled-customer-success-lead","json_url":"https://alion.io/job/contactmonkey-scaled-customer-success-lead.json","meta":{"generated_at":"2026-10-21T04:14:16Z","cache_seconds":300,"methodology":"https://alion.io/methodology","terms":"https://alion.io/terms","contact":"https://alion.io/contact","api":"https://alion.io/developers","about":"Alion is a live layer of people, companies and AI agents: who they are, whether they are real and active right now, what they do and how to work with them, readable by people and by agents and paid per call.","catalog":"https://alion.io/catalog.json","usage":{"tier":"crawler_verified","counted_by":"address","units_charged":1,"used_today":6184,"day_limit":null,"remaining_today":null,"minute_limit":300,"resets_at":"2026-10-22T00:00:00Z"}},"offers":[{"id":"company.slices","title":"One company in depth, by slice","status":"live","price":{"credits":0.02,"usd":0.002,"plus_per_slice":{"credits":0.05,"usd":0.005}},"unit":"per company, plus each slice with data","note":"the employer in depth","call":{"mcp_tool":"get_company","arguments":{"id":674782},"rest":"https://alion.io/mcp/rest/get_company?id=674782"},"human":"https://alion.io/catalog?offer=company.slices&for=job%2Fcontactmonkey-scaled-customer-success-lead"},{"id":"market.stats","title":"A market slice: pay, demand and time to fill","status":"live","price":{"credits":1,"usd":0.1},"unit":"per slice","note":"pay, demand and time to fill for this role and place","call":{"mcp_tool":"market_stats"},"human":"https://alion.io/catalog?offer=market.stats&for=job%2Fcontactmonkey-scaled-customer-success-lead"},{"id":"job.search","title":"Open jobs by role, technology, place, pay and visa","status":"live","price":{"credits":0.02,"usd":0.002},"unit":"per posting in a list","note":"similar open postings","call":{"mcp_tool":"search_jobs"},"human":"https://alion.io/catalog?offer=job.search&for=job%2Fcontactmonkey-scaled-customer-success-lead"},{"id":"company.verify","title":"Is this company real and active right now","status":"pilot","price":null,"unit":"per company","request":{"url":"https://alion.io/catalog/request","method":"POST","body":"{\"offer\": \"company.verify\", \"for\": \"job/contactmonkey-scaled-customer-success-lead\", \"note\": \"what you need it for\"}"},"human":"https://alion.io/catalog?offer=company.verify&for=job%2Fcontactmonkey-scaled-customer-success-lead"}]}