workiva-cover-letter-review

Cover Letter Clinical Review

Common Issues (Both Letters)

Issue	Risk	Fix
Markdown formatting (bold, headers, rules)	Will show literally in ATS/email	Remove all markdown for final version
”≥139%“	Special character won’t render	Use “over 139%” or “139%+"
"2ד	Multiplication sign may not render	Use “2x”
Length ~450 words	Too long. Hiring managers skim. Ideal: 250-350	Cut 30%
“Dear Hiring Team”	Generic	Use name if findable (CCO Penny Ashley-Lawrence or VP CS)
Em dashes (—)	ATS risk	Replace with hyphens or rewrite

VP Letter Specific Issues

Issue	Fix
”last year” for Sustain.Life	Acquisition was June 2024. Say “in 2024” or “recently”
Bold section headers won’t render	Restructure as flowing prose
”exactly where I want to be”	Slightly needy. Remove or rephrase confidently
”exact” used twice	Vary language
”Why Workiva, why now.”	Grammatically awkward (statement with period, not question). Rewrite
”I want to work on something that matters”	Good but preachy. Tone down
Five sections = choppy	Consolidate to 3 paragraphs

Sr Director Letter Specific Issues

Issue	Fix
”caught my attention for a specific reason”	Wordy. Cut: “caught my attention because”
Bullet list	Can seem less polished at senior level. Convert to prose
Sustain.Life hook buried in paragraph 3	Move ESG/acquisition angle earlier
”I’m ready to execute”	Passive. Show don’t tell
”that’s where I thrive”	Cliché. Cut
Too many “I” statements	23 uses of “I” — rebalance toward “you/Workiva” focus

Structural Recommendation

Both letters should follow this tighter structure:

1. Hook (2-3 sentences): Why this role, why you’re relevant — lead with Sustain.Life/ESG angle
2. Proof (4-5 sentences): Your results that matter to them — NRR, transformation, financial services
3. Fit (2-3 sentences): Why Workiva specifically, what you’ll do for them
4. Close (1 sentence): Call to action

Target: 280-320 words. Under one page with generous margins.