Career Life Stories: Alessandra Sales, Ipsy

Alessandra Sales was working as an Italian tutor when a translation job led to a career in marketing ten years ago. A long way from the foreign diplomatic role her academic background had prepared her for, Alessandra talks to us about juggling her new role as a mom with running a 20-person marketing team at her former role as VP of Marketing at Smule.

What attracted you to marketing as a career path, and how did you get your start?

I came to the United States from Italy ten years ago, without a job, without a visa, and without any marketing experience. I’d done International Studies, thinking I wanted to be a foreign diplomat, even learning a number of official languages of the United Nations. When I moved to Silicon Valley, those aspirations changed as I was thrown into a completely different world.

I started teaching Italian to people in their homes just trying to make a living while I applied for jobs. I was lucky enough to come across an opportunity with NexTag, a shopping comparison site, which was looking for an Italian and Spanish speaker to localize the site for southern Europe. So that’s what I did – I helped them build the site and manage all of the localizations. Before long, I was advertising too, and my career grew from there.

What does Smule do, and can you summarize the scope of your role as the VP of Marketing there?

Music is more than just listening — music also includes creating, sharing, discovering, participating and connecting. Music is the original social network, with the power to break down barriers, touch souls, and bring people from all over the world together.

When we started in 2008, Smule was just a company with a fun name and a big dream. We wanted to bring music back to its roots and empower anyone to join in. Today, we’re a vibrant, global community of music lovers where millions of people across the world come together each day to share their passion for music, make new friends, cheer each other on, and simply have fun.

As the VP of Marketing at Smule, I’m responsible for the company’s sales and revenue as well as user growth and the growth of our subscription base. My department is responsible for all direct response, user acquisition, influencer programs, brand, community, PR, and product marketing.

You had your first baby last year - congratulations! Can you share any insight as to what it’s like for mothers returning to the workplace?

Having a new baby and a full-time career while living in a foreign country without family around to help is not exactly the ideal scenario. I must say, it was hard returning to work. I consider myself lucky (for California) that I was able to take three and a half months off, but in reality, it’s still a very short amount of time. On the other hand, I did enjoy returning to an environment where I felt I had some control over my life and schedule again.

My biggest advice for new moms returning to work is to learn how to be efficient with your time and be strict with your agendas. For me, this meant there less small talk in the kitchen, no more unnecessary meetings, and no more days with twenty “to-dos”. Now, I come into work with just 3-4 priorities, and even though my job is endless, if I’ve done what was important for that day then I can leave feeling accomplished.

One of the outcomes of becoming more efficient is that my team has become more empowered. If I don’t feel that it’s necessary for me to be part of a meeting, then I don’t attend. In turn, I lean more on the other leaders of my team to step up. In the end, I think it’s worked out well for everyone.

How has digital marketing evolved over the last 10 years?

It’s changed so much. When I started working for NexTag, desktop was the leader for advertising. Over the years, desktop has evolved to mobile websites, HTML sites and the app world has flourished. At some point, Facebook became the go-to place for digital advertising. Attribution systems were essentially non-existent for mobile back in 2008 and 2009, and now you can attribute just as well on mobile as you can on desktop. Marketing has become so much smarter and more complex with technologies like machine learning, artificial intelligence, and algorithms; the landscape keeps changing so rapidly. As a marketer, you either have to stay on top of the latest trends or risk being left behind.

I imagine it would be very difficult for someone to start marketing now, without any prior experience like I did back in 2008. Today marketing is very technical and there are so many products and networks to understand. Now we’re expecting marketers to be not only highly analytical but also highly technical. Many marketers are expected to know sequel, python, and possess some coding competency in order to build dashboards.

What marketing trends do you expect to see continue into 2019 and beyond?

I think machine learning will continue to be leveraged by marketers to help them better understand and serve their customer segments by giving them more personalized experiences. I expect there will be a lot of emphasis around multi-task attribution, a buzz word at the moment but something which hasn’t been mastered yet. From an advertising perspective, we’re seeing advertising costs get more expensive on virtually every platform. I think there is a trend for more traditional brands to move part of their budget from an offline experience to digital, and they’re getting smarter about tracking their customers’ digital buying habits. These big companies have more money than your typical startup, so we’ll continue to see them companies play a key role in the development of the digital marketing space.

What role within your marketing team is consistently difficult to hire, and what qualities do you look for in prospective candidates?

It’s hard to find great user acquisition talent. It’s a popular title in Silicon Valley but not in other markets. If you’re an international company like us at Smule, it’s very hard to hire this type of candidate outside of the Bay Area. That’s not to say it’s easy here; many candidates have a user acquisition title, but the strong ones are hard to come by.

Regardless of the type of role I’m filling within my department, I always look for someone who is driven, curious and somewhat analytical.

What is one question you always ask candidates during the interview process?

What would the person who likes you the least say about you?

I find that when candidate thinks about this question while projecting a specific person, they tend to be sincere, and I get much better responses than if I were to just say, “tell me about your weaknesses”.

What advice do you have for young marketers on a path to leadership positions?

Try to learn something new everyday, offer your mentorship, and be humble yet assertive. And practice the things that make you uncomfortable. When you get to the leadership level, you’ll undoubtedly manage people who are smarter and more specialized than you in certain areas. You must come to peace with not being most knowledgeable person in the room.

As we wrap up, what resources (books, podcasts, blogs) do you recommend to someone growing their knowledge around marketing and/or leadership?

For general business and tech knowledge I like to read the Harvard Business Review and TechCrunch, as well as listen to Andreessen Horowitz’s podcast (a16z). As far as marketing-specific resources I read App Annie reports and monthly newsletters from

Finally, what is the best way for people to connect with you?

People can reach out to me on LinkedIn.

If you enjoyed Alessandra’s career journey, please navigate here to read other stories of impressive leaders within our Silicon Valley network.