POSITION SUMMARY

As a Sr. Customer Success Manager (Sr. CSM), you will be responsible for a portfolio of accounts within our “high touch” engagement model. Your core focus will be to drive product adoption, maximize customer value, and to perform proactive activities to mitigate churn risks as well as uncover expansion opportunities. You will serve as the primary advocate for the customer and work with cross-functional teams to deliver an exceptional customer experience. Success in this role will be measured by key metrics such as revenue retention, revenue expansion, customer engagement, and account adoption outcomes.

ESSENTIAL FUNCTIONS AND RESPONSIBILITIES  

Customer Ownership & Engagement

• Manage a dedicated book of business within a high-touch engagement model, serving as the primary point of accountability for customer success.
• Build strong, trusted customer relationships through recurring weekly or monthly meetings, ongoing email and phone communication, and periodic onsite engagements.
• Multi-thread engagements within high-ARR accounts by identifying, engaging, and sustaining relationships with multiple stakeholders—including champions, administrators, and executive sponsors—to ensure continuity, alignment, and long-term partnership.
• Act as a trusted product advisor, driving sustained usage and adoption of UpKeep’s core platform and all add-on products to maximize long-term customer value.
• Share best practices related to user adoption, system administration, and maintenance workflow optimization to help customers achieve their desired business outcomes.
• Deliver value-driven engagements such as adoption check-ins, quarterly business reviews (QBRs), and tailored product walkthroughs.
• Drive consistent customer engagement across multiple channels, including email, phone, video conferencing, webinars, and onsite visits as needed.
• Conduct proactive outreach to non-engaged or at-risk accounts to assess customer needs, satisfaction, and overall partnership health.
• Complete a defined number of customer touchpoints each week (e.g., phone calls placed and meetings hosted) to maintain momentum and visibility across accounts.

AI-Enabled Execution

• Leverage AI daily to prepare for meetings, execute engagements, summarize outcomes, and deliver timely follow-ups.
• Use AI to reduce manual effort, improve efficiency, and drive consistency across the customer lifecycle
• Promote and support adoption of UpKeep’s AI capabilities by guiding customers in transforming manual workflows with UpKeep Intelligence and related AI solutions.

Revenue Retention

• Proactively monitor account health scores, usage trends, and risk indicators to identify and mitigate churn or downgrade risks.
• Rally internal executives and senior stakeholders for key renewal discussions and high-risk customer situations to reinforce partnership value and executive alignment.
• Partner closely with the Retention Team to resolve churn and downgrade requests and reinforce long-term customer value.

Revenue Expansion & Renewals

• Identify expansion opportunities through proactive discovery and make strategic recommendations for plan upgrades, additional users, or additional products.
• Collaborate with the Sales team to support renewal confirmations and expansion motions, particularly within high-ARR accounts.

Cross-Functional Collaboration & Process Improvement

• Partner with Technical Support, Professional Services, Sales, and Product teams to address customer needs and deliver a seamless, high-quality customer experience.
• Contribute to the continuous improvement of internal processes, playbooks, and standard operating procedures.

TRAVEL

• Ability to travel up to once per quarter for customer onsite visits.

EXPERIENCE  

• Bachelor's Degree a plus in business, communications, or similar field 
• 2+ years experience in a customer-facing customer success or account management role
• Experience with Salesforce
• Experience with being measured by Gross Revenue Retention, Net Revenue Retention, or similar metrics
• Experience with a previous cloud-based or SaaS company

KNOWLEDGE

• Ability to honor deadlines and follow through on commitments
• Outstanding prioritiztaion, organization, and time management skills
• Strong written and verbal communication skills. Ability to manage multiple streams of communication
• Strong web presentation skills
• Basic technical aptitude to understand how to troubleshoot issues and provide effective solutions
• Possess ability to diagnose non-technical issues and prescribe next steps
• Possess ability to set clear expectations with customers 
• Possess ability to be assertive but empathetic during customer interactions
• Skillful at managing relationships
• Possess basic business acumen to understand how business principles relate to customer success

DESIRED BEHAVIORS 

• Self-starter that thrives in fast-paced environments
• Works well with others
• Receptive to change – is flexible. Seeks and adopts improved approaches and processes.
• Initiates action – is results oriented, takes responsibility for actions and outcomes. Meets commitments and strives for high performance.
• Manages the workload - makes timely decisions, prioritizes effectively, solves problems, monitors results and takes remedial action where necessary.
• Technically proficient – able to apply the technical knowledge and skills required in the job role and responsibilities in order to achieve the expected outputs. 
• Takes responsibility for their own learning - knows personal strengths, recognizes development needs, and takes action to improve. Is open to feedback and always seeks to learn. 
• Communicates ideas – respectfully exchange information and proposes a way forward. Listen to views of colleagues and take in diverse perspectives. 
• Works collaboratively – shares knowledge and information, fosters teamwork and contributes to a positive work environment where people want to come to work.  
• Display ethical character and competence - acts with integrity and intent, is accountable for own actions, behaves according to the company values. 

COMPENSATION

This role will receive a competitive base salary + company bonus + variable + benefits. A variety of factors are considered when determining someone’s compensation–including a candidate’s professional background, experience, and location. Final offer amounts may vary from the amounts listed below.

The pay range for this role is $90,000 - $100,000  USD per year.

POSITION SUMMARY

UpKeep has strong roots with the practitioners and managers who run day-to-day maintenance operations. The next phase of growth requires earning the attention and trust of the directors, VPs, and C-suite leaders who control budget, drive strategic decisions, and champion platforms across their organizations.

The Brand & Content Marketing Manager will lead that shift. This role owns how UpKeep shows up across every owned channel: the website, content, social, video, and webinars. The mandate is to build a brand that resonates with executive-level buyers without losing the credibility we’ve earned with the frontline audience who uses and advocates for the product every day.

This is a high-ownership role for someone who can think at the strategic level, write and create at a high standard, and build programs that scale.

ESSENTIAL FUNCTIONS AND RESPONSIBILITIES  

Executive Audience Development

• Build and execute a content strategy designed to reach and resonate with director, VP, and C-suite buyers in asset-intensive industries.
• Develop thought leadership positioning for UpKeep that speaks to operational efficiency, capital planning, and digital transformation at the leadership level.
• Create and run a webinar program targeting executive audiences: recruiting guest speakers, building co-branded content, and ensuring programs are tied to pipeline.
• Work with the team to identify the right tone, formats, and channels that earn executive attention without alienating the practitioner base.

Website & Digital Experience

• Own the end-to-end experience of upkeep.com, including site structure, messaging, navigation, UX, and design consistency.
• Manage all product pages to clearly communicate value and differentiate UpKeep at both the operator and decision-maker level.

Content Strategy & Creation

• Develop and execute a content roadmap spanning blog, customer stories, video, and branded design, using AI to accelerate research, briefing, and first-draft production.
• Prioritize formats that build credibility with executive buyers: in-depth reports, benchmark data, executive interview series, and webinar recordings.
• Use AI tools to accelerate content repurposing across channels, turning a single webinar or report into blog posts, social clips, email copy, and more without proportional increases in headcount.
• Ensure all content reflects a consistent brand voice that works across the buying committee, from the technician to the CFO.

SEO & Organic Growth

• Own UpKeep’s SEO strategy and execution: keyword targeting, on-page optimization, backlink development, and traffic performance reporting, leveraging AI tools to identify opportunities and automate analysis at scale.
• Vet, select, and manage SEO vendors or agencies where relevant.
• Tie SEO work to measurable outcomes including traffic growth, lead volume, and pipeline attribution.

Social & Brand

• Maintain and evolve UpKeep’s presence on LinkedIn, YouTube, and emerging channels.
• Build coordinated brand campaigns that connect across blog, social, video, and webinar programs.
• Develop an executive social strategy, including content that supports UpKeep leaders building their own thought leadership presence.

Team & Cross-Functional Work

• Define content workflows, publishing cadences, and internal review processes, building AI into production steps to increase team output without sacrificing quality.
• Partner closely with Product Marketing on launches, campaigns, and positioning.
• Work with Sales and Customer Success to source customer stories and identify executive reference opportunities.
• Coordinate external partners (Web, SEO, designers, production vendors) to execute key programs.

EXPERIENCE

• 5+ years in content marketing, brand, or digital marketing, with at least 2 years in B2B SaaS or a comparable enterprise software environment.
• Demonstrated experience creating content that targets senior buyers: directors, VPs, or C-suite personas.
• Experience planning and running webinar programs, including executive-level events.
• Track record of growing organic traffic and building content programs from a strategy through to execution.
• Demonstrated current use of AI tools in content production, research, or SEO workflows. Be ready to talk through how you use them and what the output difference looks like.

KNOWLEDGE 

• Strong editorial judgment with the ability to write and edit at a high standard across multiple formats and audience levels.
• Deep understanding of content SEO, including keyword research, on-page optimization, and how content drives pipeline.
• Comfortable with data: able to pull insights from analytics platforms, build a content performance report, and use data to make decisions.
• Hands-on experience with CMS platforms, marketing automation, SEO tools, and AI writing and research tools. Active use of AI in your current workflow is required, not a plus.
• Strong project management skills and a clear track record of shipping work on time across multiple concurrent priorities.
• Ability to translate technical product capabilities into language that resonates with executive and operational audiences.

How We Measure Success

• Growth in executive-level engagement: webinar attendance, content downloads, and engagement from director+ personas.
• Website traffic growth: organic sessions, returning visitors, and on-site conversion rates.
• Content output and quality: publishing cadence, traffic per piece, backlinks earned. AI-assisted workflows are expected to meaningfully raise volume without adding headcount.
• Webinar program performance: number of programs run per quarter, attendance, and pipeline influence.
• Video metrics: YouTube growth, views, and engagement by content type.
• SEO health: keyword rankings, organic visibility, and search-driven pipeline contribution.
• Customer story output: number of published case studies and executive references per quarter.

DESIRED BEHAVIORS 

• Takes ownership of outcomes, not just outputs. Knows the difference between shipping content and building a program that moves the business.
• Thinks about the full buyer journey, from an executive’s first touchpoint through to a sales conversation.
• Brings a point of view. Has opinions on what the brand should stand for and is comfortable advocating for that position.
• Communicates clearly across teams and seniority levels, internally and externally.
• Manages up well: flags blockers early, provides clear status updates, and asks the right questions when priorities need to be set.
• Stays curious about the industry, the customer, and the craft of content and brand.
• Acts with integrity and holds themselves accountable for the quality and impact of their work.
• Receptive to change – is flexible. Seeks and adopts improved approaches and processes.
•  Initiates action – is results oriented. Takes responsibility for actions and outcomes. Meets commitments and strives for high performance.
• Manages the workload - makes timely decisions, prioritizes effectively, solves problems,   monitors results, and takes remedial action where necessary.
• Technically proficient – able to apply the technical knowledge and skills required in the job role and responsibilities in order to achieve the expected outputs. 
• Takes responsibility for own learning - knows personal strengths, recognizes development needs, and takes action to improve. Is open to feedback and always seeks to learn. 
• Communicates ideas – respectfully exchanges information and proposes a way forward. Listen to views of colleagues and take in diverse perspectives. 
• Works collaboratively – shares knowledge and information, fosters teamwork, and contributes to a positive work environment where people want to come to work.  
• Display ethical character and competence - acts with integrity and intent, is accountable for own actions, behaves according to the company values. 
• Act as a good citizen of UpKeep.

COMPENSATION

This role will receive a competitive base salary + annual bonus + benefits + equity. A variety of factors are considered when determining someone’s compensation–including a candidate’s professional background, experience, and location. Final offer amounts may vary from the amounts listed below.

The pay range for this role is $125,000 - $145,000 USD per year.

POSITION SUMMARY 

We are hiring a strategic, data-driven, and action-oriented Director of Growth to own and scale our revenue engine across the full funnel. This senior role goes beyond campaign execution, you will set the demand strategy, own the budget, and scale programs across all digital channels, events, ABM, and outbound initiatives. You will partner closely with Sales, Product Marketing, and Leadership to ensure marketing activity translates into business outcomes, while building a repeatable, AI-powered growth engine.

This role is ideal for a senior marketing leader who thrives in fast-paced environments, knows how to balance experimentation with discipline, and has a track record of building pipeline programs at scale.

ESSENTIAL FUNCTIONS AND RESPONSIBILITIES  

• Own pipeline creation at scale: Set the demand generation strategy to consistently deliver MQLs, SAOs, and revenue-generating opportunities.
• Budget ownership: Manage and optimize a multimillion-dollar demand gen budget across digital, field, and ABM campaigns.
• Campaign leadership: Direct the execution of integrated campaigns across paid media, events, webinars, email nurture, ABM, SEO, and partnerships.
• Performance optimization: Establish and continuously refine lead scoring, routing, and follow-up SLAs in close collaboration with Sales leadership.
• Data-driven rigor: Build dashboards and frameworks for CPL, CAC, pipeline contribution, win rates, and ROI by channel; present results regularly to executive leadership.
• Innovation and experimentation: Drive a culture of rapid testing—scaling what works, cutting what doesn’t—and champion new approaches such as PLG campaigns, consulting partnerships, and AI-enabled engagement.
• Team leadership: Mentor and grow a high-performing demand gen team; instill best practices in campaign operations, experimentation, and cross-functional alignment.
• Event and ABM strategy: Oversee in-person and digital events as well as account-based initiatives that accelerate pipeline for mid-market and enterprise accounts.
• AI integration: Lead the adoption of AI in marketing workflows—leveraging it to accelerate content, improve targeting, and optimize campaign performance.

EXPERIENCE  

• 8–10+ years of B2B SaaS marketing experience with direct ownership of demand generation; proven success in mid-market and enterprise segments.
• Track record of building and scaling integrated demand programs that deliver measurable pipeline and revenue growth.
• Deep expertise across multiple channels: paid digital, ABM platforms (6sense, Demandbase), SEO, and email automation.
• Strong analytical skills; proven ability to manage attribution, forecasting, and reporting within Salesforce, HubSpot/Marketo, and Excel.
• Demonstrated experience managing multi-million-dollar budgets and presenting performance outcomes to executives.
• Skilled at building and leading teams; proven ability to align Sales, Marketing, and Product stakeholders around shared pipeline goals.
• Comfort with AI and emerging technologies to enhance campaign velocity and creativity.

DESIRED BEHAVIORS 

• Experience launching ABM programs from the ground up.
• Background in scaling demand generation in high-growth SaaS environments.
• Hands-on success with AI-driven marketing experimentation.

COMPENSATION 

This role will receive a competitive base salary + annual bonus + benefits + equity. A variety of factors are considered when determining someone’s compensation–including a candidate’s professional background, experience, and location. Final offer amounts may vary from the amounts listed below.

The pay range for this role is $170,000 - $185,000 USD per year.