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Talent Overview
Anna Flowers: Director of Business Operations
- Background - Led Franchise Help, a B2B online lead generator with over 200 clients and several million in annual revenue.
- Experience - Managed all aspects of business including GTM, sales, account management, marketing, and development teams.
- Personality - Data-driven, proactive problem-solver, committed to learning and personal growth.
- Other - Skilled at translating among teams and distilling complex data into actionable strategies.
Flags
🟢 Strong experience in scaling online B2B operations.
Led Franchise Help through significant growth, managing multiple departments and driving profitability.
🟡 Prefers implementation over visionary thinking.
Excels at executing ideas and refining them for real-world application, but may not be the source of innovative concepts.
🔴 No specific experience in ed-tech or test preparation.
While experienced in online businesses, lacks direct exposure to Elemental Prep's specific industry.
Recommendation
✅ Advance Anna to a long interview.
Seems like a sharp, data-driven professional. Comes across as intelligent and operationally savvy. Worth exploring how she navigated her career shift to gauge adaptability.
Chiefly Recommendation
Anna Flowers is a great fit:
- Grew with Franchise Help from early days to GM - she's seen it all
- Hands-on experience: account management, tech (GitHub tickets), growth marketing
- Ran the whole show as GM - finances, team management,
- Bootstrapped company background - she gets lean, profitable growth
Highlights:
- Can do it all - from daily ops to big picture strategy
- Built and managed teams effectively
- Deep dive in online business growth - email, A/B testing, etc
- Adapted to multiple roles as the company grew
Account Management at Mrs. Dressy (00:07 - 03:18)
- First job out of school in e-commerce formal wear
- Managed relationships with 150-200 designers
- Handled inventory updates and backend operations
- Discovered talent for working with custom backend admin systems
"I began to understand that I had a unique talent for working with custom backend admin systems and working directly with high level engineering folks to create systems that worked really well." (01:53)
Early Days at Franchise Help (03:30 - 10:32)
- Joined as 6th full-time employee in a small WeWork space
- Initial role: accounts and operations for lead generation
- Worked closely with CTO on system improvements
- Company growth: doubled headcount within a year
Growth Marketing at Franchise Help (15:48 - 26:24)
- Transition from operations to marketing for growth opportunities
- Strengths: Email marketing, SMS campaigns, product improvements
- Challenges: Disliked Facebook and Google ad management
- Key achievement: Implemented new email funnels and A/B testing
"Where I really was able to contribute as a growth marketer was less on the day-to-day programmatic, although I did understand how that worked quite well. I just wasn't the one who was going to make the fantastic new groundbreaking ads." (17:44)
Director of Client Services and Product (32:18 - 43:38)
- Managed sales and account management teams
- Focused on new product development
- Unofficial deputy role to the GM
- Balanced client services and product improvement
General Manager of Franchise Help (43:54 - 01:05:54)
- Took over as GM in February 2020, just before the pandemic
- Managed through COVID-19 challenges, including revenue loss
- Implemented remote work, leading to increased productivity
- Focused on financial management and reporting to founders
"By the end of that year, end of 2020, margin was back to positive, revenue was, back up and was, surpassed where we had been at the beginning of the year before the pandemic hit." (47:55)
Transition and Departure (01:05:54 - 01:17:25)
- Company took first round of funding, new CEO joined
- Managed transition to new leadership
- Misalignment on business priorities led to departure
- Stayed on in consulting capacity to ensure smooth transition
Current Career Goals and Future Outlook (01:17:39 - 01:23:21)
- Took intentional year-long break for personal projects
- Seeking new challenges in business operations
- Interested in high-ambiguity, high-visibility roles
- Looking for long-term commitment with growth opportunities
"I love a CEO who has thoughts, that I would never have come up with on my own, but they don't know how to make them work in the real world. I know how to make them work in the real world." (01:23:00)
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100 Day Plan - Document
View in new tabRoles and Responsibilities (00:03:26 - 00:09:38)
- Adapts to evolving roles and acts as a key liaison between leadership levels
- "Eli was the CEO at the metric level, but also the general manager of one of our partner companies. He was the first line of defense I'd call when having an issue." [00:06:16]
Strengths and Weaknesses (00:09:38 - 00:17:37)
- Self-aware about strengths in execution rather than high-level ideation
- "I'm not an ideas guy. I don't dream big ideas in the shower. I work through tiny details, like what Excel sheet I need to fix. I work through details in my head." [00:15:51]
Challenges and Future Goals (00:23:20 - 00:29:34)
- Reflects on difficult feedback and learns from challenging situations
- "The toughest feedback was from our new CEO. He perceived that I didn't know how to manage up. This is probably part of why we didn't end up continuing to work together." [00:18:37]
Navigating Business Strategy and Ethics (00:37:49 - 01:01:51)
- Balances business growth with quality and integrity in decision-making
- "We had this twinge when things were really rolling, thinking, we need to see how this goes on quality whenever we see the quantity really kick up that way." [00:57:34]
Questions About the Role and Company (01:01:51 - 01:27:40)
- Probes about the nature of the partnership Ellen is seeking
- "It sounds like she wants a partner to think through stuff with her, build, and sit next to her. Does she want someone who sits on a similar level, or more of an employee?" [01:08:43]
Skills
Business Strategy
What is your mental model/framework for business?
I tend to see a business through two complementary lenses: 1) product and client, which informs the story around the business and 2) data and KPI's, which help draw quantifiable boundaries around the story and track changes over time.
When thinking about business decisions I find it important to run everything through both lenses. If something makes a lot of financial sense but would harm the product, it probably isn't the right fit. Likewise if something would be amazing for customers, but the data shows that it would hurt us financially, it likely needs adjustments.
