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workiva-job-prep

11 min read

Workiva Job Application Prep

VP Customer Success / Senior Director Enterprise Customer Success

Prepared: February 2026
Target Roles:

  1. VP Customer Success (R11416)
  2. Senior Director of Enterprise Customer Success (R11207)

1. COMPANY BRIEFING

Company Overview

AttributeDetails
Founded2008 (as WebFilings LLC in California)
HeadquartersAmes, Iowa, USA
TickerNYSE: WK (Class A) - Russell 2000 Component
Employees~2,828 (2024)
Revenue$739M (2024)
Net Income-$55M (2024)
Total Assets$1.4B (2024)
CEOJulie Iskow (since April 2023, previously COO)
CFOBarbara Larson
Chief Customer OfficerPenny Ashley-Lawrence (EVP)

Key Historical Milestones:

  • 2008: Founded as WebFilings by Jerry Behar and team
  • 2014 (July): Renamed to Workiva LLC
  • 2014 (December): IPO on NYSE
  • 2019: Expanded to Frankfurt, Paris offices
  • 2021 (August): First acquisition - OneCloud (integration platform)
  • 2021 (December): Acquired AuditNet
  • 2023 (February): Julie Iskow succeeds Marty Vanderploeg as CEO
  • 2024 (June): Acquired Sustain.Life (carbon accounting) for ~$100M
  • 2025 (September): Launched Workiva AI agentic platform

Mission Statement

“Power transparent reporting for a better world”

Core Products & Platform Capabilities

The Workiva Platform is a cloud-based, AI-powered SaaS platform for transparent, assured, connected reporting. Key capabilities:

  1. Financial Reporting

    • SEC filings (10-K, 10-Q, S-1, 8-K, etc.)
    • XBRL/iXBRL tagging
    • Multi-entity consolidation
    • Financial close automation
    • IPO preparation

  2. Sustainability/ESG Reporting

    • CSRD/ESRS compliance
    • ISSB standards alignment
    • GRI, SASB, TCFD, CDP frameworks
    • Carbon accounting (Workiva Carbon - via Sustain.Life)
    • Double materiality assessments
    • Scope 1, 2, 3 emissions tracking

  3. Governance, Risk & Compliance (GRC)

    • SOX compliance
    • Internal controls management
    • Internal audit management
    • Enterprise risk management
    • Policy management

  4. Workiva AI (Agentic AI - launched Sept 2025)

    • Intelligent Finance (disclosure drafting, peer benchmarking)
    • Intelligent GRC (control analysis, risk identification)
    • Intelligent Sustainability (materiality assessments, ESRS alignment)
    • Specialized LLMs (Google, AWS/Anthropic, Microsoft/OpenAI)

Key Platform Differentiators:

  • Data linking - Single source of truth across all reports
  • Real-time collaboration - Multi-user concurrent editing
  • Audit trail - Complete version control and data lineage
  • 70+ pre-built connectors (Oracle, Salesforce, Workday, BlackLine, Persefoni)
  • Security - Enterprise-grade, SOC certified

Target Customers & Use Cases

Primary Buyers:

  • CFOs and Finance teams
  • Chief Sustainability Officers
  • Internal Audit teams
  • Risk/Compliance Officers
  • Legal/Governance teams

Customer Segments:

  • Fortune 1000 companies (major presence)
  • Public companies (SEC filers)
  • Private companies preparing for IPO
  • European companies (CSRD/ESEF compliance)
  • Financial services (Banking, Insurance, Investments)
  • Energy & Utilities
  • Government & Higher Education

Industries Served:

  • Banking & Investments
  • Insurance
  • Energy & Utilities
  • Government
  • Higher Education & Nonprofit

Recent Major Announcements (2024-2025)

Positive Developments:

  1. Sustain.Life Acquisition (June 2024) - $100M acquisition of carbon accounting startup, significantly bolstering ESG capabilities
  2. Workiva AI Launch (Sept 2025) - Major agentic AI platform release with specialized capabilities for finance, GRC, and sustainability
  3. IDC MarketScape Leader (2025) - Named Leader in ESG Reporting and Compliance Management
  4. Verdantix Green Quadrant Leader - Named Leader for ESG Reporting and Data Management Software
  5. G2 Leadership - Ranked leader in audit management, policy management, ERM, and sustainability management
  6. Forrester TEI Study - 204% ROI demonstrated for unified platform users
  7. Amplify 2025 Conference - Successful global conference in Washington DC and Barcelona

Regulatory Tailwinds:

  • CSRD implementation driving European demand
  • ISSB standards adoption accelerating globally
  • California climate disclosure laws creating US momentum
  • SEC climate disclosure rules (despite some delays/rollbacks)

Potential Challenges/Concerns:

  • Net loss of -$55M in 2024 (not yet profitable)
  • Stock volatility (tech/SaaS sector headwinds)
  • Intense competition in rapidly evolving ESG space
  • Regulatory uncertainty around SEC climate rules

Competitive Landscape

Direct Competitors:

  1. Workiva vs. SAP - SAP Sustainability Control Tower
  2. Workiva vs. Wolters Kluwer - CCH Tagetik for regulatory reporting
  3. Workiva vs. IBM - Envizi for ESG
  4. Workiva vs. Persefoni - Carbon accounting (though also a partner)
  5. Workiva vs. Sphera - ESG management
  6. Workiva vs. Watershed - Climate software
  7. Workiva vs. ServiceNow - GRC/Risk management

Workiva’s Competitive Advantages:

  • First-mover in SEC reporting automation (XBRL expertise since 2008)
  • Unified platform spanning finance + sustainability + GRC
  • Deep regulatory expertise and compliance track record
  • Strong audit trail and assurance capabilities
  • Established Fortune 1000 customer base

2. INDUSTRY & COMPANY CHALLENGES

Publicly Acknowledged Challenges (From Company Sources)

From 10-K/SEC Filings & Earnings:

  1. Path to Profitability - Continued investment in growth has delayed profitability; -$55M net loss in 2024
  2. Subscription Revenue Concentration - Heavy reliance on subscription renewals and expansion
  3. International Expansion Costs - Significant investment required for EMEA growth (offices in Frankfurt, Paris, Amsterdam, London)
  4. Talent Competition - Tech talent market remains competitive, especially for AI/ML specialists
  5. Customer Retention Focus - Net Revenue Retention is a key metric they emphasize

From Leadership Statements:

  1. AI Integration Complexity - CEO Julie Iskow has discussed challenges of responsibly integrating AI while maintaining data security
  2. Regulatory Pace - Managing product development against constantly shifting regulatory timelines (CSRD delays, SEC uncertainty)
  3. Customer Education - Helping customers understand the complexity of new sustainability regulations

Challenges Ascribed by Media/Analysts

External Observations:

  1. Valuation Concerns - SaaS multiples have compressed; questions about growth vs. profitability tradeoff
  2. ESG Market Fragmentation - Many point solutions emerging; risk of commoditization
  3. Sustainability Reporting Fatigue - Some companies questioning ROI of extensive ESG programs amid political/regulatory uncertainty
  4. AI Competition - Large tech players (Microsoft, Google, Salesforce) adding AI to existing platforms
  5. CSRD Delays - European CSRD implementation delays could slow near-term revenue growth
  6. US Political Risk - Potential rollback of climate disclosure requirements under changing administrations

3. APPLICATION PREP

Key Keywords & Concepts for CV/Cover Letter

Must-Include Terms:

  • Customer Success Management at scale
  • Enterprise/Strategic accounts
  • Net Revenue Retention (NRR)
  • Customer health scores / Customer 360
  • Executive business reviews (EBRs) / QBRs
  • Value realization / Time to value
  • Customer journey mapping
  • Upsell/expansion revenue
  • Churn reduction / Retention strategies
  • Cross-functional collaboration (Sales, Product, Services)
  • Digital-touch / scaled CS programs
  • Customer advocacy / Voice of Customer

Workiva-Specific Terminology:

  • Financial reporting / SEC reporting
  • ESG/Sustainability reporting (MAJOR alignment with Clarity AI!)
  • CSRD / ESRS / ISSB frameworks
  • GRC / Internal Audit / SOX compliance
  • XBRL / iXBRL
  • Connected data / Single source of truth
  • Assured integrated reporting
  • “Amaze our customers” (company value)
  • “Signature Customer Experience”

Skills & Experience That Would Resonate

Your Unique Value Proposition (Clarity AI → Workiva):

  1. ESG/Sustainability Expertise ⭐ MAJOR ADVANTAGE

    • You understand the sustainability reporting landscape intimately
    • Direct experience with CSRD, ISSB, SFDR, EU Taxonomy
    • Know the pain points of ESG data collection and reporting
    • Can speak credibly to Chief Sustainability Officers

  2. Financial Markets Knowledge

    • Asset managers and asset owners are Workiva customers
    • You understand investment workflows and regulatory requirements
    • Experience with financial services compliance

  3. Customer Success Leadership

    • Building/scaling CS organizations
    • Enterprise account management
    • Driving NRR and reducing churn
    • Executive relationship management

  4. Domain Expertise Advantage

    • You can help Workiva’s CS team become smarter about sustainability
    • Bridge between technical platform and evolving ESG regulations
    • Thought leadership potential (content, speaking, customer advisory)

What to Emphasize:

  • Scale: How large was your CS portfolio? ARR managed? Team size?
  • Results: NRR improvements, churn reduction, expansion revenue
  • Enterprise: Experience with Fortune 500 / large enterprise accounts
  • Change management: Building processes, playbooks, systems
  • Cross-functional: Working with Product, Sales, Services
  • Industry expertise: ESG/sustainability credentials
  • Global: Experience with EMEA/international customers

Likely Reporting Structure

VP Customer Success would likely report to:

  • Penny Ashley-Lawrence - EVP, Chief Customer Officer
    • Background: 20+ years experience, previously at LogMeIn and Citrix
    • Oversees: Customer Success, Services, Support, Operations, Enablement

Senior Director Enterprise CS would likely report to:

  • VP of Customer Success (this role or equivalent)
  • OR directly to Penny Ashley-Lawrence

Peer Leaders You’d Work With:

  • Michael Pinto - EVP, Chief Revenue Officer (Sales)
  • Deepak Bharadwaj - EVP, Chief Product Officer
  • Yasser Mahmud - EVP, Chief Marketing Officer
  • Mike Rost - SVP, Chief Strategy Officer & Head of IR

Company Culture Signals & Values to Mirror

Core Values (from careers page):

  1. Win as a Team - No lone heroes; collaboration
  2. Make a Positive Impact - Bring best self, affect the world positively
  3. Innovate Fearlessly - Don’t follow status quo, operate with urgency
  4. Amaze Our Customers - Simplify the complex, delight beyond expectation
  5. Do the Right Thing - Compassion, clarity, confidence in decisions

Leadership Principles:

  • Accountability - Own your commitments
  • Communication - Open and candid exchange
  • Respect - Dignity and setting others up for success
  • Empathy - Understanding others’ perspectives
  • Collaboration - Leverage each other’s strengths
  • Inclusion - Diverse community where everyone belongs
  • Trust - Believe in each other’s capabilities

Culture Signals to Emphasize in Interviews:

  • Transparency (it’s their mission!)
  • Collaboration over individual heroics
  • Customer obsession
  • Innovation and willingness to change
  • Data-driven decision making
  • Sustainability as genuine purpose (not just product)

4. INTERVIEW STRATEGY

Company-Specific Insights to Get an Interview

In Your Cover Letter/Application:

  1. Lead with ESG Alignment

    “Having spent [X years] at Clarity AI helping financial markets participants navigate ESG reporting and regulatory compliance, I was immediately drawn to Workiva’s mission of powering transparent reporting. Your recent Sustain.Life acquisition and CSRD capabilities represent exactly the intersection where I can add unique value.”

  2. Demonstrate Platform Understanding

    • Reference the “connected data” philosophy
    • Mention the unified platform spanning finance, sustainability, and GRC
    • Note the Workiva AI launch and its implications for customer success

  3. Show Customer Success Results

    • Quantify NRR, churn reduction, expansion revenue
    • Mention experience with enterprise/Fortune 500 accounts
    • Reference building/scaling CS teams

  4. Reference Recent Wins

    • Mention Verdantix and IDC MarketScape recognition
    • Reference Amplify conference if you can demonstrate awareness
    • Note the Forrester TEI study (204% ROI)

What to Emphasize to Pass Interviews

Round 1: HR/Recruiter Screen

  • Cultural fit with values
  • Career trajectory and why Workiva
  • Salary expectations alignment
  • Genuine interest in mission

Round 2: Hiring Manager (likely Penny Ashley-Lawrence or VP CS)

  • Leadership philosophy and style
  • Building/scaling CS teams
  • Handling enterprise customer escalations
  • Cross-functional collaboration examples
  • Vision for Customer Success at Workiva

Round 3: Cross-Functional Peers (Sales, Product, Services)

  • Collaboration examples
  • How you partner with Sales on renewals/expansion
  • Product feedback loop management
  • Customer escalation handling

Round 4: Executive/Final Round

  • Strategic vision
  • Market/industry insights (ESG advantage here!)
  • Leadership presence and communication
  • Cultural addition

Key Themes to Weave Throughout:

  1. Customer-centricity - Use “Amaze our customers” language
  2. Data-driven - Show you measure and optimize
  3. Collaborative - “Win as a team” examples
  4. Innovative - Show you challenge status quo
  5. Domain expertise - Your ESG knowledge is a superpower

Questions to Ask That Show Deep Knowledge

For Penny Ashley-Lawrence (CCO):

  1. “With the Sustain.Life acquisition and Workiva AI launch, how is the CS organization evolving to support customers through these new capabilities?”
  2. “What’s the current relationship between your CS team and product development on the sustainability side—especially with CSRD timelines shifting?”
  3. “How does the Signature Customer Experience program differentiate Workiva’s approach to customer success?”

For VP CS / Hiring Manager:

  1. “How is the CS org structured—by segment (enterprise/mid-market), by solution (finance/ESG/GRC), or by region?”
  2. “What does ‘success’ look like for this role in the first 90 days vs. 12 months?”
  3. “What’s the current state of digital/scaled CS programs vs. high-touch for enterprise accounts?”
  4. “How do you measure and drive Net Revenue Retention, and where are the biggest opportunities?”

For Cross-Functional Peers:

  1. “How does CS partner with Sales on the renewal process—where does handoff happen?”
  2. “What’s the feedback loop between CS and Product for feature prioritization?”
  3. “With AI becoming central to the platform, how are you thinking about customer enablement and adoption?”

Demonstrating Industry Knowledge:

  1. “With CSRD phase-in timelines and the recent EFRAG guidance updates, how are you seeing customer priorities shift?”
  2. “How do you segment customers who use Workiva primarily for financial reporting vs. those adopting the full platform including sustainability?”
  3. “What’s the competitive dynamic when customers are also evaluating point solutions like Persefoni or Watershed for specific use cases?”

Known Interview Process Details

Based on Glassdoor/General SaaS Patterns:

Typical Process:

  1. Phone screen with HR/Recruiter (30-45 min)
  2. Hiring manager interview (45-60 min)
  3. Panel interviews with cross-functional stakeholders (3-4 interviews)
  4. Final round with executive (CCO or CEO for VP-level)
  5. Possibly a case study or presentation

What to Prepare:

  • 90-day plan or “first 100 days” vision
  • Customer Success metrics you’ve driven (NRR, churn, NPS, CSAT)
  • Examples of scaling CS teams and programs
  • Escalation management examples
  • Cross-functional collaboration stories
  • Your vision for AI in Customer Success

Likely Case Study/Presentation Topics:

  • “How would you structure the CS org to support [scenario]?”
  • “A major customer is unhappy—walk us through your approach”
  • “Design a customer health score framework for Workiva”
  • “How would you drive adoption of Workiva AI across the customer base?”

ADDITIONAL RESOURCES TO REVIEW BEFORE INTERVIEWS

  1. 10-K Annual Report - Review risk factors and MD&A sections
  2. Amplify Conference Content - Watch keynotes and sessions if available
  3. Workiva Blog - Read recent posts on CSRD, AI, customer success
  4. ESG Talk Podcast - Listen to understand their thought leadership
  5. Penny Ashley-Lawrence’s LinkedIn - Understand CCO’s background and posts
  6. Glassdoor Reviews - Check recent interview experiences
  7. G2 Reviews - Understand customer sentiment and pain points
  8. Forrester TEI Study - Understand the quantified value proposition

SUMMARY: YOUR COMPETITIVE ADVANTAGES

AdvantageHow to Leverage
ESG/Sustainability expertiseYou understand the regulatory landscape and customer pain points better than most CS leaders
Financial markets experienceAsset managers/owners are key Workiva customers
Current market knowledgeCSRD, ISSB, SFDR—you know these inside out
Customer Success leadershipProven track record scaling CS organizations
Mission alignmentGenuine passion for transparency and sustainability

Your Pitch in One Sentence:

“I bring a rare combination of deep sustainability/ESG domain expertise from Clarity AI with proven Customer Success leadership, uniquely positioning me to help Workiva’s customers navigate the complex and rapidly evolving landscape of assured integrated reporting.”

Good luck, Adam! Your ESG background is a genuine differentiator—lean into it heavily.

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