From Visioning the Life you Want to Living the Life you Want

In the fall of 2018, destiny brought me to a retreat that would prove to be nothing short of transformative. Nestled in the breathtaking landscapes of Sonoma, California, a group of remarkable women from across the country congregated for a workshop called “Create the Work you Love,” hosted by Vanessa Loder, a renowned leadership and mindfulness coach and author.

Little did I know then, the profound resonance this gathering would have, not just for me but for every woman there, forging bonds that would last a lifetime.

Turning Dreams into Reality

Fast forward six years from that life-altering weekend, and what were only dreams for many of us have become tangible realities. It all began with a weekend of envisioning the lives we wanted and charting a course to manifest them. I now own and run a recruiting business that allows me to help others find careers they love and many of the other women I met have gone on to create meaningful, impactful careers. 

Most recently, I stumbled upon a LinkedIn post from a friend and fellow retreat attendee, Allyson Letteri, announcing the impending launch of her new book. I was transported back to that cozy Sonoma house where Allyson gleamed with excitement as she discussed her creative aspirations, particularly around writing. Today, those dreams have become her reality.

A Conversation with Allyson

I had the privilege of sitting down with Allyson to revisit her journey over the past six years and understand the catalysts behind her dreams of becoming a published author.

Reflecting on Our Goals

As we reminisced about our time in that Sonoma cottage, we recollected the exercise where we were asked to jot down the things that mattered most to us in life and work. For both of us, those pivotal words were “time-freedom” and “purpose”. The delicate balance of these two ideas resonate deeply with many working parents.

Turning Dreams into Reality

Could you share with us how these aspirations have taken shape in your life?

Yes! I loved my corporate and startup career, but I found it was increasingly hard to balance as my kids got older and became more involved in activities. They’ve got busy lives too! Two years ago as my daughter was about to start Kindergarten, I decided to make a change that I’d been contemplating for years: leaving my full-time job and starting my own marketing advising business.

A few things led me there. First, I really love helping build purpose-driven companies. I found that the “zero-to-one” stage was my favorite and developed a skillset in building marketing teams and functions from scratch. I did this at Thumbtack with the Pro Marketing team for three years, then I really wanted to build from the ground up again and joined Handshake as VP of Marketing in 2019. In both cases, I grew the teams to over a dozen people who managed the full funnel of marketing functions. This skillset, which combines the need to create a strategy from a blank page AND execute with limited resources, is very valuable for startups.

As I was considering what to do after Handshake, I knew I did not want to build a team from scratch for the third time in a row, especially as my family’s schedule got busier and more complex. The first year of a new job like that is particularly brutal because you are creating the strategy, doing a lot of the work on your own, and hiring at the same time. Two times back-to-back felt like enough.

But, I was eager to help other founders and startup leaders tackle these challenges. VC’s who backed Thumbtack and Handshake were occasionally asking me to have a quick call with a founder to discuss who to hire next, or how to do effective product marketing or discuss other strategic issues. I realized there is a real gap for technical leaders who have important, costly marketing decisions to make, but don’t yet have marketing expertise in-house. I increasingly felt conviction that I could build an advising business to fill that gap, so I decided to make the leap in September 2021 and become a solopreneur.

Back to your original question, this move to becoming a marketing advisor to tech startup leaders maximized two things:

    • Time freedom: I set my own schedule and generally only work while my kids are in school. I am able to spend the afternoons with them, block days for other activities, and truly turn off during school breaks and holidays
    • Purpose: I get to do work I love, which is to help founders build effective marketing teams and strategies so their innovative (often life-changing) products can make an impact in our world. I get to use my unique talents and only accept projects and clients that are aligned with my skillset and sense of purpose.

One other note: I considered leaving my full-time job and becoming an advisor both when I left Intuit and when I left Thumbtack. But in both cases, I felt like getting more experience and learning from more business scenarios would open more doors in the long run. I think this was very important in my successful transition to an advisor! There is no substitute for being an operator and building a breadth and depth of experience in a range of areas. This has made me a stronger fit for a wider range of companies, and it helps me take on more fulfilling work.

The Evolution from Marketing Leadership to Authorship

Over the last decade, you’ve had an impressive career moving from marketing leadership to advisory work, and now, to the exciting realm of publishing. What has this journey been like for you?

It’s been an exciting journey with twists and turns, and has ultimately led me to a role and a business that I can see building and enjoying for many years!

My first job out of college (I grew up in NC and Atlanta, and went to UNC-Chapel Hill) was at the Boston Consulting Group in San Francisco. I had interned at a startup in Silicon Valley during college and knew I wanted to start my career there. I wanted a job that maximized learning, opened doors, and would enable me to be financially independent. I was a business major and consulting was very attractive, and I was thrilled when I got the job. I quickly became immersed in the Sales and Marketing practice area, focused on Consumer Goods and Retail companies. I had incredible mentors and a string of travel projects that took me to Denver, Seattle, and Portland all week.

My time at BCG really lit the spark that made me a marketer. My favorite days of my job were doing consumer research. I flew all over the country for different clients, where I did things like “secret shopping” with customers in a sporting goods store and interviewing young professionals about their preferred choice in wine labels. I also ran and analyzed many surveys. I loved developing the customer empathy needed to make smart marketing decisions. I went to business school at Stanford (a dream) and returned to BCG for two more years.

As I was considering what to do next, my husband and I got the chance to move to Hong Kong for his work. We seized the opportunity and I was fortunate to get my first marketing-focused job at Intuit. I spent two years in Asia, focused on building and launching new products for small business owners in India. Then we moved back to San Francisco and I led a team in the UK and Canada to launch Intuit’s first mobile payments products in those markets. These experiences gave me incredible, hands-on go-to-market experience. Once again, my favorite days were spent in the field with small business owners, from travel agency owners in back alleys of Mumbai to mini Cooper tour operators cruising through London. 

My final job at Intuit (after I had my son and needed to slow the travel) was running retention marketing for QuickBooks at their headquarters. While I learned a lot from this marketing experience, including the importance of customer marketing to increase retention and growth, I really missed the smaller startup-like environment of the country offices. That’s what led me to actually find a role at a startup after having my second child. In particular, I wanted to continue working with small business owners and have the chance to build a function from scratch.

That led me to Thumbtack, a marketplace for consumers to hire a wide range of local service professionals for home projects, events, and more. I build the Pro Marketing team from just me to a team of 15+ people across a wide range of functions. We made progress in every area of the business, from acquiring new types of pros to rewarding our highest-performing pros with a new loyalty and rewards program. After three years, I was ready for a new challenge. And while I considered advising, I decided one more leadership experience would really open up doors down the road. I was excited to join Handshake as VP of Marketing, where I immediately led a brand refresh, launching an entirely new visual brand identity for the company. I also build the student marketing team from the ground up and during my 2.5 years there we saw millions of college students join and use the platforms to find internships and jobs.

Both Thumbtack and Handshake were purpose-driven companies, and I really loved the role my teams played in helping people find jobs and build livelihoods that created opportunity and fulfillment in their lives. The range of marketing and team management challenges I faced in all three companies prepared me to help startup leaders think about short and longer-term decisions as they build out their marketing strategy. I have years of in-the-trenches experience to draw from, which I think makes me a more practical and realistic advisor to the startups I work with today.

The Inspiration Behind Your Book

What drove you to the path of becoming an author? Can you tell us about the driving force behind your desire to write and publish a book?

Well, first of all, I have always been creative and enjoy taking on big projects. So I have probably always had the idea of writing a book in the back of my mind, but I did not know when it would happen or what the goal would be. I finally found that fit last year!

After years of building marketing functions at tech startups, and then advising early-stage startup founders, I saw a pattern. Startup leaders struggled to define an effective marketing strategy until they developed strong product messaging. They needed to be able to articulate what their product is, who it’s for, and why it’s different and better than alternative solutions. Many times, startup leaders felt overwhelmed and confused about where to start.

As their advisor, I’ve led dozens of startup leaders through a process to develop their messaging and then a full-funnel marketing strategy. I wanted to capture the essential steps in a way that would help my clients AND so that more founders and startup leaders could access and follow this process. I considered a range of types of content to create: workshops (which I love), blog posts, videos, online courses, etc. 

Then last fall, something clicked and I started thinking about capturing everything in a book. I loved the idea of being able to share the full end-to-end process. And I knew that once I had the book, I could splice it up into a huge range of content pieces if I wanted to, so the book would open more content doors as well. I began researching self-publishing and quickly got the sense that it was actually achievable to write a book in a year. So I started outlining and took it step by step.

The real driving force behind my desire to write the book is to share my knowledge and process that I have seen over and over positively impact company growth. I wanted more entrepreneurs, who may not have access to high-quality advice or a manageable process, to benefit. The book is filled with templates and very practical guidance. I really want startup leaders to be able to take action, even if they don’t have a marketing background. 

I also believe that helping innovative startups succeed matters to all of us. I’ve had the opportunity to work with startups who are building life-changing and world-changing products in a wide range of categories: health care, climate, productivity, education, small business, diversity, equity and inclusion, and more. Their innovations have the potential to substantially improve their customer lives, and impact society more broadly. I wrote this book to help more of those teams and their big ideas succeed. It’s something I am uniquely positioned to do, and I felt the passion to address an unmet need that is holding back too many startup founders. 

Unveiling Your Book

Could you provide us with a glimpse into your book and what it’s all about?

“Standout Startup: The Founder’s Guide to Irresistible Marketing That Fuels Growth” gives startup founders and leaders a clear process to develop effective product messaging and high-converting content to increase customer acquisition and retention. I’ve found that this was a frequent stumbling block for many founders, especially before they have a marketing team.

The book is divided into three parts and is filled with templates and step-by-step guidance:

You’ll start with Part 1: Define your 3 Ps to Unlock Messaging. Your 3 Ps (persona, positioning, and personality) are the three main elements you need to be able to develop effective product messaging that attracts and converts your ideal customers:

  1. Persona:  who is your ideal customer and how can you describe your product in a way that’s valuable to them?? 
  2. Positioning: how is your product different and better than alternative solutions? Why is it their best choice
  3. Personality: what are your brand attributes and how are you consistently communicating with your ideal customer in a way that builds affinity?

Once you know these elements you can move into Part 2: Develop Powerful Product Messaging. “Standout Startup” walks you through how to develop the three main components of effective messaging:

  • USP: a headline about what your product is, who it’s for, the big outcome you promise, and how it’s different and better than other solutions
  • Value propositions: the top benefits your product delivers. These are the main messages your ideal customer needs to know to choose your product 
  • Proof points: validation that your product is effective, including key product features, social proof, and data to show you can deliver the results you promise

This messaging framework is the backbone of your marketing strategy because it clarifies the most effective messages to attract and convert your ideal customers. Once you know this, you can move into Part 3: Create a Content Strategy That Drives Growth. This is where you build your marketing strategy for each stage of the customer journey. This included attracting and converting new leads, as well as onboarding and engaging customers. The content customers need to make decisions and feel motivated to take action are different in each phase. These chapters walk you through how to create and launch an effective marketing plan.

By the end of the book, you’ll have a clear, powerful messaging strategy and all the tools to create the right content. This will lead to customer growth, revenue growth, and team alignment. You’ll learn the essentials of marketing and accelerate your growth.

Key Takeaways for Your Readers

Are there specific lessons or insights you hope your readers will glean from your book?

There are lots of lessons, but here are a few gems:

  • It’s very difficult to create an effective marketing strategy if you don’t know how to describe your product and its value to your ideal customers. To develop messaging, you have to start with the 3 Ps: persona (who is your ideal customer and what are their needs?), positioning (how is your product different and better than other solutions they could choose?), and personality (how will you communicate in a way that builds affinity with your ideal customer?). This is the foundation of your marketing strategy.
  • Most of your marketing should focus on showing your ideal customers how your product and brand create value in their lives. Knowing what your ideal customers need and desire is the root of smart marketing decisions. The more customer empathy you have, the more powerful you can make your messaging and content strategy.
  • Positioning is a critical element of effective messaging and marketing. Get very clear on how your product is different and better for your ideal customer than the alternatives. The top two things you need to communicate in your marketing to help customers make a decision to buy your product is (1) why your product is valuable to them (2) why it’s a better choice than the other solutions they’re considering.
  • Always start with goals before you begin developing a marketing content and channel strategy. Right now is it more important to get more new customers interested in your product, or convert your leads at a higher rate, or drive more active use among your current customers? Depending on your answer, you’ll focus on very different types of content and channels to reach and influence your customers. Starting with goals drives focus and clarity.

Words of Wisdom for Career Transition

Having traversed this transformative journey over the past six years, what is one piece of advice you’d impart to others navigating a career transition?

At each step, ask yourself: what are my values, and what are my top criteria for any job I select? Getting clear on what you’re optimizing for in your next role will help you focus on the right options and decisions, and confidently say no to opportunities that are not a fit. For me, at different times these have included things like:

  • Gain people-management experience and grow as a people-leader
  • Focus on specific functional experiences to gain new skill sets
  • Work on a product and with a customer group that I feel passionate about 
  • Have the shortest commute possible and must be in San Francisco
  • Achieve time flexibility so I can have control over my schedule

Going back to how we started the conversation, it’s so important to feel connected to the purpose of your work, even if it’s simply building certain skills to open doors in the future. In short, be intentional and discerning about what moves you make, and then be open to the exciting surprises that come with that preparation.

Allyson’s book, “Standout Startup: The Founder’s Guide to Irresistible Marketing That Fuels Growth” is a fantastic read for anybody looking to drive growth within their organization, regardless of the size.