Be Bold Podcast—Episode 5: Lead With Your Strengths

0:00 foreign

0:03 you know I often look back at that time

0:05 and say it was probably the most

0:06 difficult decision of my entire career

0:09 to step away from a career I had just

0:12 launched the as400 product line I was

0:15 one of the top countries uh experts in

0:20 the architecture of the as400 I I was

0:23 the person who launched it in Boston I

0:26 was young this was heady stuff and so to

0:29 to make a decision at such a height to

0:32 walk away was very difficult

0:35 [Music]

0:44 hello everyone and welcome to another

0:47 episode of be bold

0:49 today I have the pleasure of speaking

0:52 with Ann Del Santo an inspirational

0:54 leader who has trailblazed throughout

0:56 her career while also prioritizing

0:59 family

1:01 today we talk about her journey hurdles

1:04 she faced along the way the mentors that

1:07 inspired her

1:08 and the advice she has for young people

1:10 building their own carriers

1:13 welcome to the podcast Anne it's a

1:15 pleasure to have you today

1:17 and full disclosure for the audience you

1:19 know and Del Santo who joins us today

1:22 is a member of the board of directors at

1:24 Juniper Networks she's an inspirational

1:26 leader in the tech world

1:29 but she started off in New York from

1:32 your accent I can tell you're from New

1:33 York but tell us a little bit about your

1:36 beginnings and how did you get

1:38 interested in Tech in the first place

1:41 well thank you manage

1:43 a wonderful

1:48 meetings and so it is it's great to join

1:52 you for this uh yes you definitely

1:55 picked up my new York City accent I I

1:58 grew up in Queens New York and I would

2:00 say uh the beginning of my love of tech

2:04 really began

2:06 um with an algebra class I fell in love

2:09 with algebra and geometry and I just

2:13 could not believe

2:14 um how rewarding it was to solve

2:17 problems to solve for an equation many

2:20 listening probably think that's

2:22 unbelievable but it's true and that was

2:26 really the beginning of of my love of

2:29 technology and and really solving

2:31 problems through the use of Technology

2:35 that's great algebra hmm

2:38 so from what I know I think you did your

2:41 schooling in St John's and you started

2:44 off in math with a minor in computer

2:48 science how did you get like really into

2:51 it like algebra was a great start but

2:53 math and computer science how did you

2:54 get into it

2:56 yeah I

2:58 I'd say John's because it was I paid my

3:01 way through college and so that really

3:03 you know helped me decide where I was

3:07 going to end up going to college

3:09 and my love of math through high school

3:12 made me realize that math helps you to

3:15 think through things it helps you to

3:18 prove your theories and and come up with

3:21 a solution and I thought it was the best

3:23 preparation at the time I was actually

3:25 thinking I might want to be a lawyer and

3:27 so I said what what could I major in

3:30 undergraduate that's going to prepare me

3:32 for the rigors of putting together a

3:34 case and I could think of nothing better

3:36 than uh you know proving a calculus

3:39 theorem and advanced calculus in physics

3:42 and so I did that it was a concentration

3:45 you had two choices in math you could go

3:47 applied or Theory and at the time

3:50 Applied Mathematics was computer science

3:52 and that was really my first

3:54 Taste of programming developing and

3:58 again solving Solutions with technology

4:00 and just the rewarding feeling when you

4:03 see that output come out based on your

4:06 program so it just it kept in

4:09 interesting me and and and getting me

4:12 excited about what laid ahead

4:14 beautiful Theory and from Theory you

4:17 move to applied math

4:18 and

4:20 if I look at math as a whole then going

4:22 into computer science these are not

4:24 areas which was typically

4:26 female dominated areas in the past it is

4:29 predominantly male dominated areas so

4:31 when you can't do this did you have any

4:34 early mentors how was it getting into

4:35 this field which is predominantly male

4:37 dominated at that time and did you have

4:39 any early mentors or anybody to help you

4:41 through this journey

4:43 yeah I would say uh you know looking

4:46 back at the time I just loved math so

4:48 much I never really actually lifted my

4:50 head up and looked around to see there

4:52 weren't very many of me in the room but

4:55 I did have two great girlfriends and we

4:57 were the only three that were in that

4:58 graduating class of math but um I also

5:02 had an older sister uh Regina and she

5:05 ended up majoring in math we both had

5:07 this love she went into Actuarial

5:09 sciences and more on the business side

5:11 but I I always had somebody that I could

5:15 share this love with and that it was

5:17 reflected back to me that that this was

5:20 fun and interesting

5:23 um and I could have a social life as

5:24 well so so that so that really did

5:28 continue to encourage me

5:30 you had a great role model your elder

5:32 sister that's awesome

5:34 after school you know getting before

5:37 getting into a profession I think you

5:39 had told me earlier that you know you

5:41 had a brief snippet where you actually

5:42 work for your dad you know your dad in

5:45 the accounting profession and you did

5:46 work for your dad and there were some

5:47 early experiences which came out of

5:49 working for your dad and maybe some

5:51 areas you definitely want to be in and

5:53 some areas you definitely do want to be

5:54 in right there was some formative period

5:56 for you do you want to share a little

5:57 bit about that

5:59 sure like you said my dad was in

6:01 accounting he he did various roles on

6:04 Wall Street and one summer I I worked in

6:07 an accounting department in a brokerage

6:09 firm

6:10 for me with my dad being an accountant

6:12 and me loving math I just thought

6:15 everybody becomes an accountant you know

6:17 when you're in school you have no idea

6:19 but after working that summer in what is

6:23 the back office I realized this is not

6:26 something I want to do the rest of my

6:28 life and when I was developing and

6:32 programming in college I likened it to a

6:35 back office job and so while I wasn't

6:37 quite sure what I was going to do with

6:39 this computer science love

6:42 I knew that sitting in front of a screen

6:45 and developing all day

6:47 um I I just couldn't see myself doing

6:50 that I didn't know what else a career

6:52 would hold for me but because of this

6:55 accounting experience I knew that

6:58 development might not be in the cards

7:00 for me

7:01 so accounting had an influence no

7:03 software development I don't want to be

7:05 sitting in front of a computer so then

7:07 you ended up in IBM so how did that IBM

7:11 journey start you know how did you

7:12 progress in the IBM Journey

7:15 sure I I had the opportunity to be an

7:18 intern for IBM in my final summer at

7:20 college and this is happenstance and

7:23 sometimes this happens in careers you

7:25 know just these lucky happenstance I was

7:29 um assigned to a systems engineer of

7:31 course I never knew what this role was I

7:33 didn't even know it existed

7:35 but I worked with a systems engineer all

7:37 summer we visited customers throughout

7:40 Manhattan I ended up by the end of the

7:43 summer giving presentations at the

7:45 customer Visitor Center on capacity

7:48 planning and how do you manage memory

7:51 and swapping and disk capacity on your

7:53 mainframes

7:55 and this combination of technology to

7:58 solve business problems working with

8:01 customers understanding their businesses

8:04 and helping them see how technology is

8:07 the solver of these problems

8:10 I almost could not believe that people

8:12 would pay you to do a job like this and

8:15 I really did fall into it as an intern

8:17 so I began working for IBM and you know

8:21 as they say the rest is history this

8:24 pre-sales systems engineering solution

8:27 engineering really became the model for

8:30 for what most of my career was made up

8:32 of

8:33 so what I hear from you is that you

8:35 loved engaging with you know customers

8:37 solving problems you know different sort

8:40 of Applied math in terms of actually

8:42 solving problems but not sitting in

8:44 front of the computer right which is

8:45 what you hated the most

8:47 so I think you spent a few years at IBM

8:52 and then you took a break

8:55 to spend time with the family to start a

8:57 family you had kids and it was a big

9:01 Hiatus if I'm not mistaken do you want

9:04 to tell us something something about

9:06 that decision as well as coming back to

9:09 work later

9:10 sure

9:12 um you know I often look back at that

9:14 time and say it was probably the most

9:15 difficult decision of my entire career

9:18 to step away from a career I had just

9:22 launched the as400 product line I was

9:25 one of the top countries uh

9:28 experts in the architecture of the as400

9:32 I I was the person who launched it in

9:34 Boston I was young this was heady stuff

9:37 and so to to make a decision at such a

9:40 height to walk away was very difficult

9:43 but I I knew that it was right for me

9:47 and our family for me to do that and so

9:50 I did stay home uh eight years to raise

9:53 my two children and then did come back

9:57 into the workforce I hadn't met anybody

9:59 who had done that at that time and I

10:02 came back as a Solutions engineer for

10:04 Oracle which you know isn't isn't known

10:08 for its uh touchy feely you know soft

10:13 culture

10:15 um but but I was grateful for that

10:17 opportunity and and I I picked up my

10:20 career at Oracle

10:22 I mean there's a lot of things you kind

10:24 of you know to unpack right there from

10:27 what you said you were on a meteoric

10:29 rise at IBM and then you had to make a

10:31 decision okay family is more important

10:33 and a lot of female leaders go through

10:36 the same kind of question in their lives

10:38 you know when they are actually doing

10:39 really well and they have to make a

10:41 choice this or that and in your example

10:43 I think you're a shining example that

10:45 it's not a choice you can do both you

10:47 can actually take a Hiatus and most

10:49 people typically worry like you know if

10:51 you are out for a while and I think you

10:54 were out for about eight years and you

10:56 just came back and you didn't miss a

10:57 Beat right so and you're not entering a

10:59 company which is a easy company to enter

11:02 you know it's a very hard charging

11:05 toughest Nails company Oracle right so

11:07 you made the transition fairly

11:09 seamlessly is there any insights you can

11:12 share with you know female leaders who

11:14 are going through the same kind of

11:15 question in their life you know am I

11:17 going to miss out on something I have to

11:19 choose between one and two and how can I

11:21 re-enter the workforce in a way it's

11:23 comfortable and possible

11:30 most things in life that are worth doing

11:32 are difficult right it was difficult to

11:35 step away it's difficult to enter in

11:38 um your confidence is takes a real hit

11:41 but I I guess two things

11:44 um always having a learner's attitude uh

11:46 being a lifelong learner coming back and

11:49 saying you know what I'm going to learn

11:51 this latest technology that we're in and

11:54 I looked for the Unity of where I could

11:56 bring immediate value you know sometimes

11:59 if you look really different than

12:00 anybody else I was a little older I had

12:03 been out of the workforce

12:05 that actually also makes me unique and

12:08 so I look at my background and say but

12:09 what can I uniquely bring to this

12:12 opportunity

12:13 and at the time db2 IBM's db2 database

12:17 was a fierce competitor and so I knew

12:20 IBM competitive intelligence because I

12:23 had worked there and so I began to teach

12:26 at Oracle what are some of the

12:28 weaknesses or the competitive

12:30 differentiators that we could bring to

12:32 customers with our new 8i database

12:35 product and that gave me a place where I

12:38 could stand in confidence something that

12:41 other people did not have but that I did

12:43 have and I could bring that and then

12:45 about six months in there was a job

12:48 opportunity that opened for a team lead

12:50 and I thought you know

12:53 um I'm probably not going to get it but

12:55 I'm going to regret it if I don't at

12:57 least try and in the interview they

13:00 asked me have you ever been a manager

13:01 and I said no I haven't but you know

13:04 what I've been a mom and I think it's

13:07 pretty similar I've had to break up

13:10 fights I've had to have people work

13:12 together find the strengths move forward

13:15 uh you know it made the director at the

13:18 time laugh but I also got the job and

13:21 and so that was just another you know

13:23 don't hold yourself back don't second

13:26 guess go for things and if the answer is

13:29 no it's okay that's the season and

13:31 you're going to learn from that

13:32 experience and go on to something else

13:35 definitely I see you know you have this

13:39 you know Clarity in terms of what you

13:42 want to do you know always put the best

13:43 version of yourself doesn't matter what

13:45 the challenge is you know and you're

13:47 coming back to work started off as an

13:50 individual contributor and then

13:52 eventually became the group vice

13:54 president running all of systems

13:55 engineering in Oracle and that's not an

13:57 easy feat any learnings through that

14:00 experience you know how you grew up to

14:02 be a leader of people any mentors any

14:05 any insights or stories you can share

14:07 with our audience

14:09 sure I mean each each one of those steps

14:13 are our step and a season in your career

14:15 you start always keeping you know the

14:18 true north is our customers right we're

14:21 not a company we don't have customers

14:23 who love our products and so always

14:26 thinking about what is the best thing we

14:28 can do to have our customers fall in

14:30 love with our product and really

14:32 understand how it solves their Solutions

14:34 and bringing that to the people that

14:36 worked for me also really thinking about

14:38 career pathing for the people that were

14:41 in my organization so the internal focus

14:43 of making people love what they do every

14:46 day and feel like they're really growing

14:48 their career those were some key lessons

14:51 I learned as as my organization grew and

14:55 as as we grew to different places around

14:58 the world so um and I would say that my

15:01 mentors many times my mentors were the

15:05 leader I was reporting to I know you've

15:07 had Hillary on this podcast she was

15:09 definitely a mentor for me because while

15:13 when I started she was leading the whole

15:16 organization she always made it a point

15:19 to really get to know uh the shining

15:23 stars in her organization and I felt

15:25 very encouraged by that that you know

15:27 while she's in California and I was in

15:29 Boston she made it a point to talk with

15:32 me meet with me and those were things

15:35 that would just meant a lot as I was

15:37 building my career

15:39 um and being back in the workforce

15:42 so a New Yorker was already in

15:44 California in Oracle and then your next

15:47 Journey was to Salesforce if I'm not

15:48 mistaken in 2019 you joined Salesforce

15:51 again I think a company known for its

15:54 customer focus probably that's one of

15:55 the things which attracted you to

15:56 Salesforce and you grew in Salesforce

15:59 you're running a thousand plus people

16:00 organization hitting the products

16:03 that's a company in the peak of its

16:05 growth too at that time so what were

16:07 some of the challenges you faced what

16:08 were some of the

16:10 you know great achievements you feel

16:13 like you know you did in your journey

16:14 through Salesforce is there something

16:15 you can share with us

16:17 sure I mean Salesforce like you said

16:19 they were known for customer-centric I

16:22 think the technically the thing that

16:24 really got my attention in 2012 is I had

16:28 only been on on-premise software I had

16:30 not been I've not seen things in the

16:32 cloud and I was amazed at the power of

16:35 their platform I was amazed that every

16:38 customer was on the same version that

16:41 this is the SAS model these are things

16:43 that blew my mind back then and and I

16:46 wanted to be a part of it uh the new

16:49 challenge was taking on a global

16:51 organization dealing with customers in

16:54 every country around the world was that

16:57 new challenge that I stepped into while

17:00 I was there I also took on specialist

17:02 sales so you know a sales organization

17:06 that got me really working very closely

17:08 with product and that began

17:12 um just that really understanding

17:14 product the things that drive product

17:16 engineering product Road mapping and

17:20 that's how my final role was to lead the

17:23 platform product organization which was

17:26 which was a wonderful experience and a

17:31 lot of it was just all that years of

17:33 experience of studying customers

17:35 bringing it to our product roadmap and

17:38 really turning around the engagement

17:41 with customers from a product

17:42 perspective so that was wonderful it

17:46 also got me in a position to meet with

17:49 CEOs of isvs that we're building on our

17:53 platform and I think that was the

17:56 beginning of me realizing that working

17:59 with founder CEOs new CEOs

18:03 transformative CEOs and companies was

18:07 very exciting just sharing strategy

18:10 working on strategy uh which which I

18:13 would say was most instrumental in

18:15 laying the groundwork for the chapter

18:16 that I'm in now

18:18 hold that thought for a while I'm going

18:20 to get there I want to kind of spend

18:21 some time there but your journey is very

18:25 interesting for me because usually

18:26 you're sitting in you know the journey

18:28 to lead a product organization comes

18:30 from either you are you know in front of

18:32 the computer a lot of time in terms of

18:34 you know development or you know

18:36 Building Products you know having a

18:38 business background and then growing in

18:40 that journey and becoming a product

18:41 leader your journey is actually you

18:43 started with the customers Solutions

18:45 what does it really help to make the

18:47 solutions take in terms of specialist

18:48 sales and then eventually gone to the

18:50 product organization very different

18:51 Journey but an equally powerful journey

18:53 and you know kudos to what you achieve

18:55 in Salesforce now let's go into the

18:58 second chapter uh the chapter which you

19:00 are in right now where you're really

19:02 enjoying this role where you are in the

19:04 board of many companies you're also

19:06 working with you know founder CEOs and

19:08 you know helping them see some of the

19:10 potential you saw you know when you

19:12 worked very early in your career and

19:14 making them see where they could be how

19:16 are you enjoying this role and tell us

19:18 inside you know what's most interesting

19:21 in this role

19:22 yeah in every season of your career

19:25 there there are real highlights or or

19:28 reasons that you know I used to say to

19:30 people who worked for me what makes you

19:32 jump out of bed in the morning you know

19:34 and there's it's different and it's

19:36 Unique in every season but I would say

19:39 in this season the focus on strategy

19:42 what is the strategy to to bring growth

19:45 um how do we transform so that we're

19:48 staying one step ahead of either

19:50 technological architectural changes and

19:54 Dynamics or what have our customers

19:56 looking for uh and then that close

19:59 working relationship with CEOs new CEOs

20:03 Founders CEOs uh CEOs like the CEO that

20:07 you have at Juniper who's just amazing

20:10 this amazing career from engineering uh

20:14 to being the CEO of this incredible

20:15 company I those are the those are the

20:19 aspects of this job that I I just love

20:22 and relish being able to do that you

20:25 know every day for companies that are

20:28 making a difference in so many

20:30 businesses around and I I'm back always

20:34 to that the thing that started me in

20:36 Tech I love companies that are solving

20:39 what looks like boring problems but are

20:42 but are universally needed across the

20:45 board and uh the companies that I I work

20:48 with today

20:49 all have a different aspect of that but

20:53 but that's a key part of the companies

20:55 that I was looking for to to work for on

20:58 their board

21:00 fascinating to hear that part of the

21:02 journey I also always enjoy speaking to

21:06 you because you have these nuggets of

21:07 wisdom you know which you are able to

21:09 impart in a matter of a couple of

21:10 sentences and I really enjoy that let me

21:14 ask you for

21:16 as we kind of round out the show as an

21:18 as an advice to the new

21:21 new folks are coming to the workforce

21:23 people coming from college not sure

21:25 where they need to be which area they

21:28 need to choose what's the advice you can

21:30 give for folks coming into this field

21:34 um you know doesn't matter which

21:35 background they come from which tubers

21:37 background they come from what's the one

21:39 or two pieces of advice you can give

21:41 them to make them thrive in this you

21:43 know Wonderful era we are in right now

21:46 in the midst of chat GPT AI everything

21:48 is changing you know every moment what

21:51 would be a CH piece of advice you can

21:53 give them

21:58 career is you know number one

22:00 there are many seasons in a long career

22:04 just like there are in life and for each

22:06 season take it as it comes and make the

22:10 right decisions for those Seasons the

22:12 decisions I made as a new systems

22:15 engineer at IBM was very different from

22:18 the decisions I made as a as a young

22:20 mother in very different as the head of

22:24 platform product Global product at

22:26 Salesforce and today but these seasons

22:30 do come and when you look back on them

22:32 you you want to feel no regret about

22:36 making the right decision about the

22:37 moment you are in and trusting the next

22:40 season that it will be okay that you

22:42 know and a lot of times uh that's what I

22:46 I Mentor people to do the other thing

22:48 that I would say is sort of the secret

22:51 to what I learned is opportunity almost

22:55 always

22:56 lies where problems lie it's it's

23:00 usually alone only place there's not

23:02 many people that run to that area

23:04 but if you have the courage to run to

23:06 the area where the problems are

23:09 you'll be amazed at how much opportunity

23:12 opens up when you are solving the

23:15 complex and the difficult problems

23:17 because that's where a lot of the value

23:19 is hidden so if you can solve these

23:22 problems and bring value to your fellow

23:25 employees to your customers to the

23:27 company you work for to anybody in your

23:29 life this is this is really you know

23:32 when I look back these are the places

23:34 the times when I I hesitated because

23:37 nobody else was there it can be a little

23:40 lonely it can be a little daunting but

23:42 when I look back those tended to be the

23:45 biggest places of opportunity

23:47 um in my career and in my life so so I

23:50 would encourage anybody in your career

23:53 journey to think about those things

23:55 um because there's there is opportunity

23:57 around and abounding

24:00 brilliant

24:01 let me summarize the two points number

24:03 one

24:04 be in the moment you know put your best

24:07 work in the moment don't overthink the

24:09 future and where you need to be focused

24:12 on your best work at the problem you're

24:14 solving the second is navigate towards

24:17 problem areas because that's where the

24:18 opportunities are you know growth and

24:20 comfort don't go together so you need to

24:22 be a little bit uncomfortable to get to

24:24 those growth opportunities those are the

24:25 two Sage advice

24:27 really a pleasure to talk to you and as

24:29 always thank you for joining us today

24:32 thank you so much

24:40 so much